EP3227303B1 - Bicyclic compounds as pest controllers - Google Patents

Bicyclic compounds as pest controllers Download PDF

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Publication number
EP3227303B1
EP3227303B1 EP15801879.6A EP15801879A EP3227303B1 EP 3227303 B1 EP3227303 B1 EP 3227303B1 EP 15801879 A EP15801879 A EP 15801879A EP 3227303 B1 EP3227303 B1 EP 3227303B1
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Prior art keywords
alkyl
group
alkoxy
cycloalkyl
optionally substituted
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EP15801879.6A
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German (de)
French (fr)
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EP3227303A1 (en
Inventor
Alexander ARLT
Martin FÜSSLEIN
Silvia Cerezo-Galvez
Arnd Voerste
Thomas Bretschneider
Reiner Fischer
Peter Jeschke
Eike Kevin Heilmann
Kerstin Ilg
Olga Malsam
Peter Lösel
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Bayer CropScience AG
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Bayer CropScience AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D521/00—Heterocyclic compounds containing unspecified hetero rings

Definitions

  • the present application relates to novel bicyclic compounds, agents containing these compounds, their use for combating animal pests and methods and intermediates for their preparation.
  • the compounds of the formula (I) and also those compounds listed in Table 1 which do not fall under the formula (I) have a good activity as pesticides, for example against arthropods and in particular insects, and in addition the rule especially against crop plants are very good plant compatibility and / or have favorable toxicological and / or favorable environmental properties.
  • Aryl also as part of a larger unit, such as, for example, arylalkyl
  • Aryl also as part of a larger unit, such as, for example, arylalkyl
  • Hetaryl equivalent to heteroaryl, also as part of a larger moiety such as hetarylalkyl selected from the series furyl, thienyl, pyrrolyl, pyrazolyl, imi
  • Aryl also as part of a larger unit, such as, for example, arylalkyl
  • Aryl also as part of a larger unit, such as, for example, arylalkyl
  • Hetaryl equivalent to heteroaryl, also as part of a larger unit, such as hetarylalkyl selected from the series pyrazolyl, imidazolyl, 1,2,3-triazolyl
  • Cation for an alkali metal ion from the series lithium, sodium, potassium, rubidium, cesium preferably from the series lithium, sodium, potassium or a Beryllium, magnesium, calcium, strontium, barium alkaline earth metal, preferably magnesium, calcium, Heterocyclyl for oxetanyl, thiethanyl, tetrahydrofuryl and morpholinyl.
  • Halogen is fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine or bromine.
  • Saturated or unsaturated hydrocarbon radicals such as alkyl or alkenyl
  • heteroatoms e.g. in alkoxy, as far as possible, in each case straight-chain or branched.
  • optionally substituted radicals may be monosubstituted or polysubstituted, with multiple substituents the substituents being the same or different.
  • T in the radical A of the formula (Aa) is oxygen
  • the remainder is pyridine N -oxide derivative of the formula in front.
  • the representation of the formal charges (+ on the nitrogen and - on the oxygen) was omitted here.
  • a preferred embodiment of the invention relates to compounds of the formula (I) in which A represents the radical of the formula (Aa) stands.
  • a further preferred embodiment of the invention relates to compounds of the formula (I) in which A is pyridin-3-yl.
  • a further preferred embodiment of the invention relates to compounds of the formula (I) in which A is 5-fluoropyridin-3-yl.
  • a further preferred embodiment of the invention relates to compounds of the formula (I) in which A is pyrimidin-5-yl.
  • a further preferred embodiment of the invention relates to compounds of the formula (I) in which A is pyridazin-4-yl.
  • a further preferred embodiment of the invention relates to compounds of the formula (I) in which R 2 represents the radicals mentioned under a).
  • a further preferred embodiment of the invention relates to compounds of the formula (I) in which R 2 represents the radicals mentioned under b).
  • a further preferred embodiment of the invention relates to compounds of the formula (I) in which R 2 represents the radicals mentioned under c).
  • a further preferred embodiment of the invention relates to compounds of the formula (I) in which R 2 represents the radicals mentioned under d).
  • a further preferred embodiment of the invention relates to compounds of the formula (I) in which R 2 is the radical mentioned under e).
  • a further preferred embodiment of the invention relates to compounds of the formula (I) in which R 2 is the radical mentioned under f).
  • a further preferred embodiment of the invention relates to compounds of the formula (I) in which R 2 is the radical mentioned under g).
  • a further preferred embodiment of the invention relates to compounds of the formula (I) in which R 2 is the radical (D-2) stands.
  • the invention relates to compounds of the formula (IA)
  • the invention relates to compounds of the formula (IB)
  • the invention relates to compounds of the formula (IC)
  • the invention relates to compounds of the formula (ID)
  • the invention relates to compounds of the formula (IE)
  • the invention relates to compounds of the formula (IF)
  • the invention relates to compounds of the formula (IG)
  • the invention relates to compounds of the formula (IH)
  • the invention relates to compounds of the formula (II)
  • the invention relates to compounds of the formula (IJ)
  • the invention relates to compounds of the formula (IK)
  • the invention relates to compounds of the formula (II)
  • the invention relates to compounds of the formula (III)
  • the invention relates to compounds of the formula (IN)
  • the invention relates to compounds of the formula (IO)
  • the invention relates to compounds of the formula (IP)
  • the compounds of the formula (I) and their acid addition salts and metal salt complexes have good activity, in particular for combating animal pests, which include arthropods and in particular insects.
  • Suitable salts of the compounds of the formula (I) may be customary non-toxic salts, ie salts with corresponding bases and salts with added acids.
  • salts with inorganic bases such as alkali metal salts, for example sodium, potassium or cesium salts, alkaline earth metal salts, for example calcium or magnesium salts, ammonium salts, salts with organic bases and with inorganic amines, for example triethylammonium, Dicyclohexylammonium-, N, N '- Dibenzylethylenediammonium, pyridinium, picolinium or ethanolammonium salts, salts with inorganic acids, for example hydrochlorides, hydrobromides, dihydrosulfates, trihydrosulfates, or phosphates, salts with organic carboxylic acids or organic sulfonic acid, for example formates, acetates, trifluoroacetates, maleates, tartrates, methanesulf
  • the compounds of the formula (I) may also be present in different compositions as stereoisomers, ie as geometric and / or optical isomers or mixtures of isomers. Both the pure Stereoisomers as well as any mixtures of these isomers are the subject of this invention, although in general only compounds of the formula (I) are mentioned here.
  • the invention therefore relates to both the pure enantiomers and diastereomers, as well as their mixtures for controlling animal pests, which include arthropods and in particular insects.
  • optically active, stereoisomeric forms of the compounds of the formula (I) and salts thereof are preferably used according to the invention.
  • the substituted aminopyridines of the formula (AI) can be reacted with the corresponding activated carboxylic acids (for example as the carboxylic acid chloride or its hydrochloride) of the formula (A-II) in the presence of basic reaction auxiliaries in a first reaction step to give compounds of the formula (A-III ) are implemented. These are then replaced by appropriate sulfur donors such. B. Lawesson's reagent to compounds of formula (A-IV) thioniert. If this reaction is carried out at elevated temperature, the resulting thioamides of the formula (A-IV) can be cyclized directly to give compounds of the formula (I). Otherwise, compounds of the formula (A-IV) can be cyclized in a third reaction step in the presence of a suitable base, for example potassium carbonate, to give compounds of the formula (I).
  • a suitable base for example potassium carbonate
  • amidation reactions are carried out in the presence of a condensing agent, optionally in the presence of an acid acceptor and optionally in the presence of a solvent.
  • Suitable condensing agents are all condensing agents customarily used for such amidation reactions. Examples which may be mentioned are acid halide formers such as phosgene, phosphorus trichloride, oxalyl chloride or thionyl chloride; Carbodiimides such as N, N'- dicyclohexylcarbodiimide (DCC) and 1- (3-dimethylaminopropyl) -3-ethyl-carbodiimide (EDCI), or other conventional condensing agents such as phosphorus pentoxide, polyphosphoric acid, N, N'- carbonyldiimidazole, 2-chloropyridine 1-Methoiodide (Mukaiyamas reagent), 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ), triphenylphosphine / carbon tetrachloride, bromotripyrrolidino-phosphonium hex
  • Suitable acid acceptors are all customary inorganic or organic bases, for example triethylamine, diisopropylethylamine, N- methylmorpholine or N, N- dimethylaminopyridine. If appropriate, process A according to the invention (step 1) is carried out in the presence of a suitable reaction auxiliary, for example N, N- dimethylformamide or N, N- dimethylaminopyridine.
  • Suitable solvents or diluents are all inert organic solvents, for example aliphatic or aromatic hydrocarbons (such as petroleum ether, toluene), halogenated hydrocarbons (such as chlorotoluene, dichloromethane, chloroform, 1,2-dichloroethane), ethers (such as diethyl ether, dioxane, tetrahydrofuran , 1,2-dimethoxyethane), esters (such as ethyl acetate or methyl ester), nitrohydrocarbons (such as nitromethane, nitroethane, nitrobenzene), nitriles (such as acetonitrile, benzonitrile), amides (such as N, N- dimethylformamide, N, N- dimethylacetamides , N- methylformanilide, N- methylpyrrolidone, hexamethylphosphoric triamide) and dimethyl sulfoxide or water
  • LG COOR
  • R alkyl, aryl
  • diethylacetyl chloride, trimethylacetyl chloride and the like can be used therefor.
  • Method A - Step 2 The amide function of the carboxylic acid amides of type (A-III) can be achieved by suitable sulfurization reagents, e.g. Lawesson's reagent or phosphorus (V) sulfide, with heating in a suitable solvent, e.g. As toluene or anisole, are converted into a thioamide function, whereby compounds of the type (A-IV) are formed [cp. z. B. EP 2 560 008 for N- (2,6-dichloro-3-pyridyl) benzenecarbothioamide].
  • suitable sulfurization reagents e.g. Lawesson's reagent or phosphorus (V) sulfide
  • a suitable solvent e.g. As toluene or anisole
  • the compounds of the formula (A-IV) can be prepared by methods known from the literature (cf. EP 2 560 008 for 5-chloro-2-phenyl-thiazolo [5,4-b] pyridine) by heating in a suitable solvent, e.g. For example, toluene or DMF, in the presence of a base such as. For example, sodium hydride or potassium carbonate, in the compounds of formula (I) convert.
  • a suitable solvent e.g. For example, toluene or DMF
  • a base such as.
  • the compound 5-chloro-2- (3-pyridyl) thiazolo [5,4-b] pyridine is novel and also the subject of the invention.
  • WO 2010/008847 can be chlorinated or brominated Thiazolopyridines with optionally in situ generated substituted arylboronic acids or Arylboronklarpinakolestern in the presence of suitable coupling catalysts, such as.
  • suitable coupling catalysts such as.
  • a base such as sodium carbonate or sodium bicarbonate, in an inert solvent or diluent, such as.
  • Chlorinated thiazolopyridines can be prepared with 2- (trialkylstannyl) pyrimidines (in analogy to WO 2013/159064 ) in the presence of suitable coupling catalysts, such as tetrakis (triphenylphosphine) palladium (0) in combination with copper (I) iodide, in an inert solvent or diluent, such as 1,4-dioxane. (See also Synthesis Example (7)).
  • suitable coupling catalysts such as tetrakis (triphenylphosphine) palladium (0) in combination with copper (I) iodide, in an inert solvent or diluent, such as 1,4-dioxane.
  • Chlorinated thiazolopyridines (in analogy to Journal of Organic Chemistry (2010), 75, 8830-8832 ) can also be reacted with 2-pyridylzinc halides in the presence of suitable catalyst systems such as tris (dibenzylideneacetone) dipalladium in combination with a ligand such as 2-dicyclohexylphosphino-2 ', 4', 6'-triisopropylbiphenyl in an inert solvent or diluent , such as tetrahydrofuran, arylate. (See also Synthesis Example (8)).
  • suitable catalyst systems such as tris (dibenzylideneacetone) dipalladium in combination with a ligand such as 2-dicyclohexylphosphino-2 ', 4', 6'-triisopropylbiphenyl in an inert solvent or diluent , such as tetrahydrofuran, arylate.
  • LG SnR 3
  • the compounds of the formula (Ia) can first be converted by methods known from the literature into compounds of the formula (Ih) which are then reacted with halogen-activated heterocycles according to Reaction Scheme II (Method F) in an inert organic solvent or diluent analogously to compounds continue to react the formula (Ii) (see. WO 2009/154775 respectively. WO 2010/116282 ).
  • Suitable coupling catalysts are palladium catalysts such as [1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium (II) or tetrakis (triphenylphosphine) palladium.
  • Suitable basic reaction auxiliaries for carrying out the processes according to Reaction Scheme III are preferably carbonates of sodium or potassium.
  • Preferred diluents are nitriles, such as acetonitrile, benzonitrile, in particular acetonitrile, or ethers, such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, in particular 1,2-dimethoxyethane, in combination with water.
  • nitriles such as acetonitrile, benzonitrile, in particular acetonitrile
  • ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, in particular 1,2-dimethoxyethane, in combination with water.
  • Chlorinated heteroaromatic bicycles can be prepared by heating in the presence of optionally substituted aliphatic primary or secondary amines or arylmethyl or
  • Hetarylmethylaminen in an inert organic solvent or diluent such as.
  • dimethylformamide to compounds of the (type (1-c), (1-d) and (1-e)) implement.
  • this reaction proceeds in the presence of a suitable base such as potassium carbonate.
  • a suitable base such as potassium carbonate.
  • Optionally substituted cyclic secondary amines preferably react in the presence of suitable coupling catalysts, such as. B. Pd (OAc) 2 , and suitable ligands, such as. B. 2,2'-bis (diphenylphosphino) -1,1'-binaphthyl (BINAP), with the addition of a base such as sodium tert-butoxide and in the presence of an inert organic solvent or diluent, with chlorinated heteroaromatic Bicyclen to compounds of the formula (Id).
  • suitable solvents or diluents are all inert organic solvents, for example aliphatic or aromatic hydrocarbons. Preference is given to using aromatic hydrocarbons, for example toluene.
  • Method D With optionally substituted anilines, chlorinated heteroaromatic bicyclics in an inert organic solvent or diluent react to form the corresponding arylamino compounds of the formula (If), preferably with catalysis by suitable coupling catalysts, such as, for example, B. Pd (OAc) 2 or tris (dibenzylideneacetone) dipalladium (0), in the presence of a suitable ligand, such as. B. 2,2'-bis (diphenylphosphino) -1,1'-binaphthyl (BINAP) or 2-dicyclohexylphosphino-2 ', 4', 6'-triisopropylbiphenyl, and a base such.
  • suitable coupling catalysts such as, for example, B. Pd (OAc) 2 or tris (dibenzylideneacetone) dipalladium (0)
  • a suitable ligand such as.
  • tert-butoxide see. Bioorganic & Medicinal Chemistry 2012, 20, 5600 - 5615 for preparing tert -butyl [5 - ( ⁇ 2 - [(cyclopropylcarbonyl) amine] [1,3] thiazolo [5,4- b ] pyridin-5-yl ⁇ amino) -2-flurophenyl] carbamate and Synthesis Example ( 9)).
  • Suitable solvents or diluents are all inert organic solvents, for example aliphatic or aromatic hydrocarbons. Preference is given to using aromatic hydrocarbons, for example toluene, or alcohols, such as tert-butanol.
  • Preferred electrophiles are alkyl halides of the formula R 23 -X, in which case R 23 is in particular alkyl, cycloalkyl, alkylthioalkyl, cyanoalkyl and alkoxyalkyl and X is halogen, such as iodine, bromine or chlorine (see Synthesis Example (14)).
  • Optionally substituted heterocycles such as, for example, imidazoles, pyrazoles and triazoles, can be prepared on the basis of the literature-known method E shown in Reaction Scheme II, preferably in the presence of suitable catalysts such as copper (I) iodide, in the presence of basic ligands, eg. Trans -N, N'-dimethylcyclohexane-1,2-diamine, and a base such as potassium carbonate, in an inert organic solvent or diluent, respectively, into chlorinated bicyclic systems (see Journal of Organic Chemistry (2010), 69, 5578 , see also Synthesis Example (13)).
  • suitable catalysts such as copper (I) iodide
  • basic ligands eg. Trans -N, N'-dimethylcyclohexane-1,2-diamine
  • a base such as potassium carbonate
  • Suitable solvents or diluents are all inert organic solvents, for example aliphatic or aromatic hydrocarbons. Preference is given to using aromatic hydrocarbons such as, for example, toluene, but also more polar solvents such as DMF.
  • Method G - Step 1 Compounds of formula (Ia) can be prepared by literature methods with carbon monoxide and an alcohol, for. As methanol, with catalysis by suitable metal compounds in combination with suitable ligands such. B. palladium (II) acetate in combination with 1,3-bis (diphenylphosphino) propane, and in the presence of bases such as triethylamine or potassium carbonate, in suitable solvents such. B. the alcohol itself, THF and / or DMF, to the corresponding carboxylic acid esters of the formula (Ij) are reacted [see. WO 2007/016392 for methyl 2- (isopropylamino) thiazolo [5,4-b] pyridine-5-carboxylate].
  • Esters of the formula (Ij) can be prepared by methods known from the literature by means of suitable bases, such as. As aqueous lithium hydroxide or sodium hydroxide solution, in suitable solvents or diluents, such as. As dioxane or THF, in compounds of formula (Ik) are transferred with free acid function.
  • Method G - Step 3 Compounds of the formula (I) in which R 2 is a radical from the series (C-1) to (C-9) or -C (X) -NR 22 R 23 can be prepared from Compounds of the formula (Ik) after appropriate activation (ie LG represents an optionally in situ generated nucleofuge leaving group) can be prepared by known methods [cf. Method A, step 1].
  • Suitable condensing agents for activating the carboxylic acids of the formula (I-k) are all condensing agents customarily used for such amidation reactions.
  • Method G - Step 4 The subsequent reactions of the activated compounds of the formula (II) with the respective components according to Reaction Scheme III are optionally carried out in the presence of a suitable reaction auxiliary and in the presence of a suitable solvent or diluent.
  • Suitable reaction auxiliaries are basic reaction auxiliaries for carrying out the processes according to Reaction Scheme IV.
  • acid binders for example amines, in particular tertiary amines, and also alkali metal and alkaline earth metal compounds.
  • tertiary amines such as N- propyl-diisopropylamine or N- ethyl-diisopropylamine (DIEA, Hünig's base) are preferably used.
  • Suitable solvents or diluents are all inert organic solvents.
  • amides for example N, N- dimethylformamide, as solvent.
  • compounds of formula (Io) may be degraded by Curtius degradation, such as in Houben-Weyl, Methods of Organic Chemistry, Volume XI / 1 (Georg Thieme Verlag Stuttgart), p. 865 described, can be obtained.
  • the compounds of the formula (Ik) can react, for example, with diphenylphosphoryl azide (DPPA) in the presence of tert- butanol directly to give compounds of the formula (Io).
  • DPPA diphenylphosphoryl azide
  • the compounds of the formulas (Ip) can be obtained by N-alkylation in a first reaction step, N -diblocking (ie cleavage of the Boc group) in a second reaction step and subsequent N- acylation in a third reaction step receive.
  • the compounds of the formula (Iq) can be prepared by N- blocking (ie cleavage of the Boc group) in a first reaction step and subsequent N- acylation in a second reaction step.
  • the compounds of the formula (Ip) can also be obtained by N- alkylation from the compounds of the formula (Iq).
  • compounds of the formula (Ip) can be obtained by N- acylation of compounds of the formula (Ic).
  • acidic or basic reaction auxiliaries can be used according to the literature procedure for the removal of the protective group.
  • carbamate-type protecting groups preference is given to using acidic reaction auxiliaries.
  • the tert- butylcarbamate protective group for example, mixtures of mineral acids such as hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, phosphoric acid or organic acids such as benzoic acid, formic acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, benzenesulfonic acid or toluenesulfonic acid in a suitable diluent such as water and / or an organic solvent such as tetrahydrofuran, dioxane, dichloromethane, chloroform, ethyl acetate, ethanol or methanol.
  • ethoxyfuran ethoxysulfonic acid
  • a suitable diluent such as water and / or an organic solvent
  • Compounds of the formula (I) in which W is SO (sulfoxides) or SO 2 (sulfones) can be prepared by methods known from the literature by oxidation from compounds of the formula (I) in which W is S (thioethers), for example by an oxidizing agent in a suitable solution or Diluent.
  • Suitable oxidizing agents are, for example, dilute nitric acid, hydrogen peroxide, Oxone® and peroxycarboxylic acids, such as meta- chloroperbenzoic acid.
  • Suitable solvents or diluents are inert organic solvents, typically acetonitrile and halogenated solvents such as dichloromethane, chloroform or dichloroethane, and water and alcohols such as methanol for the reaction with Oxone®.
  • the enantiomers can also be obtained from the racemate, for example by preparative separation by means of a chiral HPLC.
  • the compounds of the formula (I) can be present as geometrical and / or as optically active isomers or corresponding isomer mixtures in different compositions.
  • These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers.
  • the invention thus comprises pure stereoisomers as well as any mixtures of these isomers.
  • the invention also relates to methods for controlling animal pests, in which compounds of the formula (I) are allowed to act on animal pests and / or their habitat. Preference is given to the control of animal pests in agriculture and forestry and in the protection of materials. Among these, preferably excluded are methods for surgical or therapeutic treatment of the human or animal body and diagnostic procedures that are performed on the human or animal body.
  • the invention further relates to the use of the compounds of the formula (I) as pesticides, in particular pesticides.
  • pest control always includes the term pesticides.
  • the compounds of the formula (I) are suitable for plant protection, favorable warm-blooded toxicity and good environmental compatibility for the protection of plants and plant organs from biotic and abiotic stress factors, for increasing crop yields, improving the quality of the crop and for controlling animal pests, in particular insects, Arachnids, helminths, nematodes and molluscs found in agriculture, horticulture, livestock, aquaculture, forestry, gardens and recreation, storage and materials protection and hygiene. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • pests include: Pests of the genus Arthropoda, in particular of the class Arachnida eg Acarus spp., Eg Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., Eg Aculus fockeui, Aculus badendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., Eg Brevipalpus phoenicis, Bryobia graminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp., Eg Eg E
  • Aulacorthum solani Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae, Brachycaudus helichrysi, Brachycolus spp., Brevicoryne brassicae, Cacopsylla spp.
  • Pemphigus spp. Eg Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Phenacoccus spp., Eg Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., Eg Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., Eg Planococcus citri, Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Eg Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseu
  • Ctenolepisma spp. Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; from the class of Symphyla eg Scutigerella spp., eg Scutigerella immaculata; Pests from the strain of Mollusca, in particular from the class of bivalvia, for example Dreissena spp .; and from the class of Gastropoda eg Arion spp., eg Arion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., eg Deroceras laeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp .
  • Animal and human parasites from the strains of Platyhelminthes and Nematoda eg Aelurostrongylus spp., Amidostomum spp., Ancylostoma spp, Angiostrongylus spp., Anisakis spp., Anoplocephala spp., Ascaris spp., Ascaridia spp., Baylisascaris spp., Brugia spp , Bunostomum spp., Capillaria spp., Chabertia spp., Clonorchis spp., Cooperia spp., Crenosoma spp., Cyathostoma spp., Dicrocoelium spp., Dictyocaulus spp., Diphyllobothrium spp., Dipylidium spp., Dirofilaria spp.
  • Dracunculus spp. Echinococcus spp., Echinostoma spp., Enterobius spp., Eucoleus spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Filaroides spp., Gongylonema spp., Gyrodactylus spp., Habronema spp., Haemonchus spp , Heligmosomoides spp., Heterakis spp., Hymenolepis spp., Hyostrongylus spp., Litomosoides spp., Loa spp., Metastrongylus spp., Metorchis spp., Mesocestoides spp., Moniezia spp., Muellerius spp., Necator spp.
  • Trichinella spp. Trichobilharzia spp., Trichostrongylus spp., Trichuris spp., Uncinaria spp., Wuchereria spp .; Plant pests from the Nematoda strain, ie plant parasitic nematodes, in particular Aglenchus spp., Eg Aglenchus agricola, Anguina spp., Eg Anguina tritici, Aphelenchoides spp., Eg Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimus spp., Eg Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus spp., Eg Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus,
  • Paratrichodorus spp. Eg Paratrichodorus minor, Pratylenchus spp., Eg Pratylenchus penetrans, Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp., Eg Radopholus citrophilus, Radopholus similis, Rotylenchulus spp., Rotylenchus spp , Scutellonema spp., Subanguina spp., Trichodorus spp., Eg Trichodorus obtusus, Trichodorus primitivus, Tylenchorhynchus spp., Eg Tylenchorhynchus annulatus, Tylenchulus spp., Eg Tylenchulus semipenetrans, Xiphinema spp., Eg Xiphinema
  • the order of the coccidia eg Eimeria spp., Can be determined from the sub-region of the protozoa. fight.
  • the compounds of the formula (I) may optionally also be used in certain concentrations or application rates as herbicides, safeners, growth regulators or agents for improving plant properties, as microbicides or gametocides, for example as fungicides, antimycotics, bactericides, viricides (including anti-viral agents) or as a remedy for MLO (Mycoplasmalike organism) and RLO (Rickettsia-like-organism). If appropriate, they can also be used as intermediates or precursors for the synthesis of further active ingredients.
  • the present invention further relates to formulations and application forms prepared therefrom as pesticides such.
  • B. drench, drip and spray liquors comprising at least one compound of formula (I).
  • the uses include other pesticides and / or effect-improving adjuvants such as penetration enhancers, e.g.
  • vegetative oils such as rapeseed oil, sunflower oil, mineral oils such as paraffin oils, alkyl esters of vegetal fatty acids such as rapeseed oil or soybean oil methyl ester or alkanol alkoxylates and / or spreading agents such as alkyl siloxanes and / or salts, e.g.
  • organic or inorganic ammonium or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate and / or retention-promoting agents such.
  • Typical formulations are, for example, water-soluble liquids (SL), emulsion concentrates (EC), emulsions in water (EW), suspension concentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR) and capsule concentrates (CS). ;
  • SL water-soluble liquids
  • EC emulsion concentrates
  • EW emulsions in water
  • SC suspension concentrates
  • SC SE, SE, FS, OD
  • WG water-dispersible granules
  • GR granules
  • capsule concentrates CS
  • the formulations contain, in addition to one or more compounds of the formula (I), further agrochemical active substances.
  • auxiliaries such as extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, antifreeze agents, biocides, thickeners and / or further auxiliaries, for example adjuvants.
  • An adjuvant in this context is a component that enhances the biological effect of the formulation without the component itself having a biological effect.
  • Examples of adjuvants are agents that promote retention, spreading behavior, adherence to the leaf surface, or penetration.
  • formulations are prepared in a known manner, e.g. by mixing the compounds of the formula (I) with auxiliaries, such as, for example, extenders, solvents and / or solid carriers and / or further auxiliaries, for example surface-active substances.
  • auxiliaries such as, for example, extenders, solvents and / or solid carriers and / or further auxiliaries, for example surface-active substances.
  • the preparation of the formulations is carried out either in suitable systems or before or during use.
  • Excipients which can be used are those which are suitable for the formulation of the compounds of the formula (I) or the use forms prepared from these formulations (such as, for example, ready-to-use pesticides such as spray liquors or seed dressings), such as certain physical, technical and / or biological properties To give properties.
  • polar and non-polar organic chemical liquids e.g. from the classes of aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also be substituted, etherified and / or esterified), ketones (such as acetone, cyclohexanone), Esters (including fats and oils) and (poly) ethers, simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethylsulfoxide).
  • aromatic and non-aromatic hydrocarbons such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes
  • alcohols and polyols which may also be substituted, etherified and / or esterified
  • ketones such as
  • Suitable liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g.
  • Petroleum fractions mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • alcohols such as butanol or glycol and their ethers and esters
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • Suitable solvents are, for example, aromatic hydrocarbons, e.g. Xylene, toluene or alkylnaphthalenes, chlorinated aromatic or aliphatic hydrocarbons, e.g. Chlorobenzene, chloroethylene, or methylene chloride, aliphatic hydrocarbons, e.g. Cyclohexane, paraffins, petroleum fractions, mineral and vegetable oils, alcohols such as e.g. Methanol, ethanol, iso-propanol, butanol or glycol and their ethers and esters, ketones such as e.g. Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents such as dimethyl sulfoxide and water.
  • aromatic hydrocarbons e.g. Xylene, toluene or alkylnaphthalenes
  • chlorinated aromatic or aliphatic hydrocarbons e
  • Suitable carriers are in particular: for example, ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock flour, such as finely divided silica, alumina and natural or synthetic silicates, resins, waxes and / or solid fertilizers. Mixtures of such carriers can also be used.
  • Suitable carriers for granules are: eg broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, paper, coconut shells, corn cobs and tobacco stems.
  • liquefied gaseous diluents or solvents can be used.
  • Examples of emulsifying and / or foaming agents, dispersants or wetting agents having ionic or non-ionic properties or mixtures of these surfactants are salts of polyacrylic acid, salts of lignosulphonic acid, salts of phenolsulphonic acid or naphthalenesulphonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, with substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic acid esters, taurine derivatives (preferably alkyl taurates), phosphoric acid esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols and derivatives of the compounds containing sulphates, sulphonates and phosphates, eg Alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates, protein hydroly
  • dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and nutrient and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • inorganic pigments e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and nutrient and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • Stabilizers such as cold stabilizers, preservatives, antioxidants, light stabilizers or other chemical and / or physical stability-improving agents may also be present. It may also contain foam-forming agents or defoamers.
  • formulations and the use forms derived therefrom may also contain, as additional auxiliaries, adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-containing polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural phospholipids such as cephalins and lecithins and synthetic phospholipids.
  • additional auxiliaries may be mineral and vegetable oils.
  • auxiliaries may be present in the formulations and in the use forms derived therefrom.
  • additives are, for example, fragrances, protective colloids, binders, adhesives, thickeners, thixotropic substances, penetration promoters, retention promoters, stabilizers, sequestrants, complexing agents, humectants, spreading agents.
  • the compounds of formula (I) may be combined with any solid or liquid additive commonly used for formulation purposes.
  • retention promoters are all those substances which reduce the dynamic surface tension such as dioctylsulfosuccinate or increase the visco-elasticity such as hydroxypropyl guar polymers.
  • Suitable penetration promoters in the present context are all those substances which are usually used to improve the penetration of agrochemical active substances into plants.
  • Penetration promoters are in this context defined by the fact that they can penetrate from the (usually aqueous) application broth and / or from the spray coating into the cuticle of the plant and thereby increase the material mobility (mobility) of the active ingredients in the cuticle.
  • the in the literature Baur et al., 1997, Pesticide Science 51, 131-152 ) method can be used to determine this property.
  • Examples include alcohol alkoxylates such as coconut oil ethoxylate (10) or isotridecyl ethoxylate (12), fatty acid esters such as rapeseed oil or soybean oil, fatty amine alkoxylates such as tallowamine ethoxylate (15) or ammonium and / or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate ,
  • the formulations preferably contain between 0.00000001 and 98 wt .-% of the compound of formula (I), more preferably between 0.01 and 95 wt .-% of the compound of formula (I), most preferably between 0.5 and 90% by weight of the compound of formula (I), based on the weight of the formulation.
  • the content of the compound of the formula (I) in the forms of application prepared from the formulations (in particular pesticides) can vary within wide ranges.
  • the concentration of the compound of the formula (I) in the use forms may usually be between 0.00000001 and 95% by weight of the compound of the formula (I), preferably between 0.00001 and 1% by weight, based on the weight of the application form , lie.
  • the application is done in a custom forms adapted to the application.
  • the compounds of formula (I) may also be used in admixture with one or more suitable fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficials, herbicides, fertilizers, avian repellents, phytotonics, sterilants, safeners, Semiochemicals and / or plant growth regulators can be used, for example, to broaden the spectrum of action, to extend the duration of action, to increase the rate of action, to prevent repellence or to prevent development of resistance. Furthermore, such drug combinations plant growth and / or tolerance to abiotic factors such. As high or low temperatures, improve against dryness or increased water or Bodensalzgehalt. Also, flowering and fruiting behavior can be improved, germination and rooting can be improved, harvesting and crop yields increased, maturity can be enhanced, crop quality and / or nutritional value increased, shelf life extended and / or crop productivity improved.
  • the compounds of the formula (I) may be present in admixture with other active substances or semiochemicals such as attractants and / or avian repellents and / or plant activators and / or growth regulators and / or fertilizers.
  • the compounds of the formula (I) can be used in mixtures with agents for improving plant properties such as, for example, growth, yield and quality of the crop.
  • the compounds of the formula (I) are present in formulations or in the formulations prepared from these formulations in admixture with other compounds, preferably those as described below.
  • drugs with unknown or ambiguous mechanism of action such as afidopyropene, afoxolaner, azadirachtin, benclothiaz, benzoximate, bifenazate, bromopropylate, quinomethionate, cryolites, cyclaniliprole, cycloxapride, cyhalodiamide dicloromezotiaz, dicofol, diflovidazine, flometoquine, fluensulfone, flufenerim, flufenoxystrobin, flufiprole, Flaxxafon, Fluopyram, Fluralaner, Fufenozide, Guadipyr, Heptafluthrin, Imidaclothiz, Iprodione, Meperfluthrin, Paichongding, Pyflubumide, Pyralidyl, Pyrifluquinazone, Pyriminostrobin, Tetramethylfluthrin
  • the compounds of formula (I) may be combined with biological pesticides.
  • Biological pesticides include, in particular, bacteria, fungi, yeasts, plant extracts, and those products formed by microorganisms, including proteins and secondary metabolites.
  • Biological pesticides include bacteria such as spore-forming bacteria, root-colonizing bacteria and bacteria that act as biological insecticides, fungicides or nematicides.
  • Bacillus amyloliquefaciens strain FZB42 (DSM 231179), or Bacillus cereus, in particular B. cereus strain CNCM I-1562 or Bacillus firmus, strain I-1582 (Accession number CNCM I-1582) or Bacillus pumilus, especially strain GB34 (Accession no. ATCC 700814) and strain QST2808 (Accession No. NRRL B-30087), or Bacillus subtilis, especially strain GB03 (Accession No. ATCC SD-1397), or Bacillus subtilis strain QST713 (Accession No. NRRL B-21661) or Bacillus subtilis Strain OST 30002 (Accession No.
  • NRRL B-50421 Bacillus thuringiensis, in particular B. thuringiensis subspecies israelensis (serotype H-14), strain AM65-52 (Accession No. ATCC 1276), or B. thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372), or B. thuringiensis subsp. kurstaki strain HD-1, or B. thuringiensis subsp. tenebrionis strain NB 176 (SD-5428), Pasteuria penetrans, Pasteuria spp.
  • fungi and yeasts which can be used as biological pesticides are:
  • Beauveria bassiana especially strain ATCC 74040, coniothyrium minitans, in particular strain CON / M / 91-8 (Accession No. DSM-9660), Lecanicillium spp., In particular strain HRO LEC 12, Lecanicillium lecanii, (formerly known as Verticillium lecanii), in particular strain KV01, Metarhizium anisopliae, in particular strain F52 (DSM3884 / ATCC 90448), Metschnikowia fructicola, in particular strain NRRL Y-30752, Paecilomyces fumosoroseus (new: Isaria fumosorosea), in particular strain IFPC 200613, or strain Apopka 97 (Accesion No.
  • Paecilomyces lilacinus in particular P. lilacinus strain 251 (AGAL 89/030550), Talaromyces flavus, in particular strain V117b, Trichoderma atroviride, in particular strain SC1 (Accession Number CBS 122089), Trichoderma harzianum, in particular T. harzianum rifai T39. (Accession Number CNCM I-952).
  • viruses that can be used or used as biological pesticides are:
  • Adoxophyes orana Apple peel winder
  • Granulosis virus GV
  • Cydia pomonella codling moth
  • Granulosis virus GV
  • Helicoverpa armigera cotton bollworm
  • Nuclear polyhedrosis virus NPV
  • Spodoptera exigua mNPV
  • Spodoptera frugiperda armyworm
  • mNPV Spodoptera littoralis
  • bacteria and fungi that are added as 'inoculant' plants or plant parts or plant organs and promote by their special properties, plant growth and plant health.
  • examples are: Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., In particular Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp., Or Gigaspora monosporum, Glomus spp., Laccaria spp.
  • plant extracts and those products formed by microorganisms, including proteins and secondary metabolites, which can be used as biological pesticides are: Allium sativum, Artemisia absinthium, Azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum, Chitin, Armor Zen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza, Fungastop, Heads Up (Chenopodium quinoa saponin extract), Pyrethrum / Pyrethrins, Quassia amara, Quercus, Quillaja, Regalia, Requiem TM Insecticide, Rotenone, Ryania / Ryanodine, Symphytum officinale, Tanacetum vulgare, Thymol, Triact 70, TriCon, Tropaeulum majus, Urtica dioica, Veratrin, Viscum album, Brassicacaeen
  • the compounds of the formula (I) can be combined with safeners, for example Benoxacor, Cloquintocet (-mexyl), Cyometrinil, Cyprosulfamide, Dichlormid, Fenchlorazole (-ethyl), Fenclorim, Flurazole, Fluxofenim, Furilazole, Isoxadifen (-ethyl), Mefenpyr (-diethyl), naphthalic anhydride, oxabetrinil, 2-methoxy-N - ( ⁇ 4 - [(methylcarbamoyl) amino] phenyl ⁇ sulfonyl) benzamide ( CAS 129531-12-0 ), 4- (dichloroacetyl) -1-oxa-4-azaspiro [4.5] decane ( CAS 71526-07-3 ), 2,2,5-trimethyl-3- (dichloroacetyl) -1,3-oxazolidine ( CAS 52836-31-4
  • Plants are understood to mean all plants and plant populations, such as desirable and unwanted wild plants or crops (including naturally occurring crops), for example cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugarcane, tomatoes , Peas and other vegetables, cotton, tobacco, oilseed rape, as well as fruit plants (with the fruits apples, pears, citrus fruits and grapes).
  • Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or can not be protected by plant breeders' rights.
  • Plant parts are understood to mean all aboveground and subterranean parts and organs of plants such as shoot, leaf, flower and root, examples of which include leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment according to the invention of the plants and plant parts with the compounds of the formula (I) is carried out directly or by acting on their environment, habitat or storage room according to the usual treatment methods, e.g. by dipping, spraying, evaporating, fogging, spreading, brushing, injecting and in the case of propagation material, in particular in the case of seed, further by single-layer or multi-layer coating.
  • plants and their parts can be treated according to the invention.
  • wild-type or plant species and plant varieties obtained by conventional biological breeding methods such as crossing or protoplast fusion and parts thereof are treated.
  • transgenic plants and plant cultivars obtained by genetic engineering, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated.
  • the term "parts” or “parts of plants” or “plant parts” has been explained above. It is particularly preferred according to the invention to treat plants of the respective commercially available or in use plant cultivars.
  • Plant varieties are understood as meaning plants having new traits which have been bred by conventional breeding, by mutagenesis or by recombinant DNA techniques. These may be varieties, breeds, biotypes and genotypes.
  • the preferred plants or plant cultivars to be treated according to the invention which are to be treated include all plants which, as a result of the genetic modification, obtain genetic material which gives these plants particularly advantageous valuable properties ("traits").
  • traits are better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to water or soil salinity, increased flowering, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products.
  • Further and particularly emphasized examples of such properties are an increased ability of the plants to defend themselves against animal and microbial pests, such as insects, arachnids, nematodes, mites, snails, causing e.g.
  • toxins produced in the plants in particular those produced by the genetic material from Bacillus thuringiensis (eg by the genes CryIA (a), CryIA (b), CryIA (c), CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryIF as well as their combinations) are produced in the plants, furthermore an increased ability to repel the plants against phytopathogenic fungi, bacteria and / or viruses, eg Systemically acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins, and increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT" gene ).
  • SAR Systemically acquired resistance
  • PAT phosphinotricin
  • transgenic plants are the important crops such as cereals (wheat, rice, triticale, barley, rye, oats), corn, soy, potato, sugar beets, sugarcane, tomatoes, peas and other vegetables, cotton, tobacco, rape, and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with special emphasis on corn, soy, wheat, rice, potato, cotton, sugar cane, tobacco and oilseed rape.
  • Traits that are particularly emphasized are the increased resistance of the plants to insects, arachnids, nematodes and snails.
  • the treatment of the plants and plant parts with the compounds of formula (I) is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, for example by dipping, (spraying) spraying (spraying), sprinkling, evaporation , Spraying, misting, sprinkling, foaming, brushing, spreading, injecting, pouring, drip irrigation and, in the case of propagating material, in particular seed, further by dry pickling, wet pickling, slurry pickling, encrusting, single or multi-layer coating, etc It is also possible to use the compounds of the formula (I) according to the ultra-low-volume method or to inject the use form or compound of formula (I) itself into the soil.
  • a preferred direct treatment of the plants is foliar application, i. Compounds of the formula (I) are applied to the foliage, wherein the treatment frequency and the application rate should be matched to the infestation pressure of the respective pest.
  • the compounds of the formula (I) also enter the plants via the root system.
  • the treatment of the plants is then carried out by the action of the compounds of formula (I) on the habitat of the plant.
  • This may be, for example, by drenching, mixing into the soil or the nutrient solution, i. the location of the plant (e.g., soil or hydroponic systems) is soaked in a liquid form of the compounds of formula (I), or by the soil application, i. the compounds of formula (I) are incorporated in solid form (e.g., in the form of granules) at the plant site.
  • this may also be by metered addition of the compound of formula (I) in a solid form (e.g., as granules) into a flooded paddy field.
  • seed treatment methods should also incorporate the intrinsic insecticidal or nematicidal properties of pest-resistant transgenic plants in order to achieve optimum protection of the seed and germinating plant with a minimum of pesticide cost.
  • the present invention therefore more particularly relates to a method of protecting seed and germinating plants from attack by pests by treating the seed with one of the compounds of formula (I).
  • the method according to the invention for the protection of seeds and germinating plants from infestation by pests further comprises a method in which the seed is treated simultaneously in one operation or sequentially with a compound of formula (I) and mixing partner. It also also includes a method in which the seed is treated at different times with a compound of formula (I) and mixing partner.
  • the invention also relates to the use of the compounds of the formula (I) for the treatment of seed for the protection of the seed and the resulting plant from animal pests.
  • the invention relates to seed which has been treated for protection against animal pests with a compound of formula (I).
  • the invention also relates to seed treated at the same time with a compound of formula (I) and mixing partner.
  • the invention further relates to seed which has been treated at different times with a compound of formula (I) and mixing partner.
  • the individual substances may be contained in different layers on the seed.
  • the layers which comprise a compound of the formula (I) and mixture partners may optionally be separated by an intermediate layer.
  • the invention also relates to seed in which a compound of the formula (I) and mixing partner are applied as a constituent of a coating or as a further layer or further layers in addition to a coating.
  • the invention relates to seed which, after treatment with a compound of the formula (I), is subjected to a film coating process in order to avoid dust abrasion on the seed.
  • One of the advantages that occurs when one of the compounds of the formula (I) acts systemically is that the treatment of the seed protects not only the seed itself, but also the resulting plants after emergence from animal pests. In this way, the immediate treatment of the culture at the time of sowing or shortly afterwards can be omitted.
  • Another advantage is the fact that by treating the seed with a compound of formula (I) germination and emergence of the treated seed can be promoted.
  • Compounds of formula (I) may also be used in combination with signal technology agents whereby better colonization with symbionts such as rhizobia, mycorrhiza and / or endophytic bacteria or fungi takes place and / or optimized nitrogen fixation occurs.
  • symbionts such as rhizobia, mycorrhiza and / or endophytic bacteria or fungi takes place and / or optimized nitrogen fixation occurs.
  • the compounds of the formula (I) are suitable for the protection of seed of any plant variety used in agriculture, in the greenhouse, in forests or in horticulture.
  • these are seeds of cereals (eg wheat, barley, rye, millet and oats), corn, cotton, soy, rice, potatoes, sunflower, coffee, tobacco, canola, rape, turnip (eg sugar beet and fodder beet), peanut, vegetables (eg tomato, cucumber, bean, cabbage, onions and lettuce), fruit plants, turf and ornamental plants.
  • cereals eg wheat, barley, rye and oats
  • corn, soya, cotton, canola, oilseed rape and rice are examples of seeds of cereals (eg wheat, barley, rye and oats), corn, soya, cotton, canola, oilseed rape and rice.
  • transgenic seed with a compound of the formula (I) is also of particular importance.
  • the heterologous genes in transgenic seed can be derived from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium.
  • the present invention is particularly useful for the treatment of transgenic seed containing at least one heterologous gene derived from Bacillus sp. comes. Most preferably, this is a heterologous gene derived from Bacillus thuringiensis.
  • the compound of the formula (I) is applied to the seed.
  • the seed is treated in a state where it is so stable that no damage occurs during the treatment.
  • the treatment of the seed can be done at any time between harvesting and sowing.
  • seed is used which has been separated from the plant and freed from flasks, shells, stems, hull, wool or pulp.
  • seed may be used that has been harvested, cleaned and dried to a moisture content that is storable.
  • seed may also be used which, after drying, e.g. treated with water and then dried again, for example priming.
  • the compounds of the formula (I) are generally applied to the seed in the form of a suitable formulation.
  • suitable formulations and methods for seed treatment are known to those skilled in the art.
  • the compounds of the formula (I) can be converted into the customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other seed coating compositions, and also ULV formulations.
  • formulations are prepared in a known manner by mixing compounds of formula (I) with conventional additives, such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and also water.
  • conventional additives such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and also water.
  • Dyes which may be present in the seed dressing formulations which can be used according to the invention are all dyes customary for such purposes. Both water-insoluble pigments and water-soluble dyes are useful in this case. Examples which may be mentioned under the names rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red 1 known dyes.
  • Suitable wetting agents which may be present in the seed dressing formulations which can be used according to the invention are all wetting-promoting substances customary for the formulation of agrochemical active compounds.
  • Preferably used are alkylnaphthalene sulfonates, such as diisopropyl or diisobutyl naphthalene sulfonates.
  • Suitable dispersants and / or emulsifiers which may be present in the seed dressing formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active compounds. Preference is given to using nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants.
  • Particularly suitable nonionic dispersants are, in particular, ethylene oxide-propylene oxide, block polymers, alkylphenol polyglycol ethers and tristryrylphenol polyglycol ethers and their phosphated or sulfated derivatives.
  • Suitable anionic dispersants are in particular lignosulfonates, polyacrylic acid salts and arylsulfonate-formaldehyde condensates.
  • Defoamers which may be present in the seed-dressing formulations which can be used according to the invention are all foam-inhibiting substances customary for the formulation of agrochemical active compounds.
  • Preferably usable are silicone defoamers and magnesium stearate.
  • Preservatives which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Examples include dichlorophen and Benzylalkoholhemiformal.
  • Suitable secondary thickeners which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Preference is given to cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.
  • Suitable adhesives which may be present in the seed dressing formulations which can be used according to the invention are all customary binders which can be used in pickling agents.
  • Preferably mentioned are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose.
  • the gibberellins are known (cf. R. Wegler "Chemie der convinced für Schweizer- und Swdlingsbekungsstoff", Vol. 2, Springer Verlag, 1970, p. 401-412 ).
  • the seed dressing formulations which can be used according to the invention can be used either directly or after prior dilution with water for the treatment of seed of various kinds.
  • the concentrates or the preparations obtainable therefrom by dilution with water can be used for dressing the seeds of cereals such as wheat, barley, rye, oats and triticale, as well as the seeds of corn, rice, rape, peas, beans, cotton, sunflowers , Soy and beets or vegetable seed of various nature.
  • the seed dressing formulations which can be used according to the invention or their dilute application forms can also be used for pickling seeds of transgenic plants.
  • the pickling is done by placing the seed in a batch or continuous mixer, adding either desired amount of seed dressing formulations, either as such or after prior dilution with water, and until the formulation is evenly distributed mix the seed.
  • a drying process follows.
  • the application rate of the seed dressing formulations which can be used according to the invention can be varied within a relatively wide range. It depends on the particular content of the compounds of the formula (I) in the formulations and on the seed.
  • the application rates for the compound of the formula (I) are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 15 g per kilogram of seed.
  • the compounds of formula (I) are active against animal parasites, in particular ectoparasites or endoparasites.
  • animal parasites in particular ectoparasites or endoparasites.
  • endoparasite includes in particular helminths and protozoa such as coccidia.
  • Ectoparasites are typically and preferably arthropods, especially insects and acarids.
  • the compounds of formula (I) which are of low toxicity to warm-blooded animals are useful in the control of parasites found in livestock and livestock in livestock, breeding animals, zoo animals, laboratory animals, experimental animals and domestic animals. They are effective against all or individual stages of parasite development.
  • Farm animals include, for example, mammals such as sheep, goats, horses, donkeys, camels, buffaloes, rabbits, reindeer, fallow deer, and especially cattle and pigs; Poultry such as turkeys, ducks, geese and, in particular, chickens; Fish and shellfish, e.g. in aquaculture and also insects like bees.
  • the domestic animals include, for example, mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets, and especially dogs, cats, caged birds, reptiles, amphibians and aquarium fish.
  • the compounds of formula (I) are administered to mammals.
  • the compounds of the formula (I) are administered to birds, namely caged birds and in particular poultry.
  • control means that the compounds of formula (I) effectively reduce the incidence of the particular parasite in an animal infected with such parasites to a harmless extent can. More specifically, “combating” in the present context means that the compound of formula (I) can kill the respective parasite, prevent its growth or prevent its replication.
  • arthropods include:
  • Metastigmata From the subclass Akari (Acarina) and the order Metastigmata, for example from the family Argasidae, such as Argas spp., Ornithodorus spp., Otobius spp., From the family Ixodidae, such as Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp. Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp.
  • Argasidae such as Argas spp., Ornithodorus spp., Otobius spp.
  • Ixodidae such as Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp. Dermacentor spp., Haemophysalis spp
  • Parasitic protozoa include:
  • Mastigophora such as Trypanosomatidae, for example Trypanosoma b. brucei, Tb gambiense, Tb rhodesiense, T. congolense, T. cruzi, T. evansi, T. equinum, T. lewisi, T. percae, T. simiae, T. vivax, Leishmania brasiliensis, L. donovani, L. tropica such as Trichomonadidae, for example Giardia lamblia, G.
  • Trypanosomatidae for example Trypanosoma b. brucei, Tb gambiense, Tb rhodesiense, T. congolense, T. cruzi, T. evansi, T. equinum, T. lewisi, T. percae, T. simiae, T. vivax, Leishmania brasiliensis, L.
  • Sarcomastigophora (Rhizopoda) such as Entamoebidae, for example Entamoeba histolytica, Hartmanellidae, for example Acanthamoeba sp., Harmanella sp .; Apicomplexa (Sporozoa), such as Eimeridae, for example Eimeria acervulina, E. adenoides, E. alabamensis, E. anatis, E. anserina, E. arloingi, E. ashata, E. aubumensis, E. bovis, E. brunetti, E canis, E. chinchillae, E. clupearum, E.
  • Sarcomastigophora Roscomastigophora
  • Rhizopoda such as Entamoebidae, for example Entamoeba histolytica, Hartmanellidae, for example Acanthamoeba sp., Harmanella s
  • parvum such as Toxoplasmadidae, for example Toxoplasma gondii, Hammondia heydornii, Neospora caninum, Besnoitia besnoitii; such as Sarcocystidae, for example Sarcocystis bovicanis, S. bovihominis, S. ovicanis, S. ovifelis, S. neurona, S. spec., S. suihominis, such as Leucozoidae, for example Leucocytozoon simondi, such as Plasmodiidae, for example Plasmodium berghei, P falciparum, P. malariae, P. ovale, P.
  • P. spec. such as piroplasmea, for example Babesia argentina, B. bovis, B. canis, B. spec., Theileria parva, Theileria spec., as Adeleina , for example Hepatozoon canis, H. spec.
  • the compounds of the formula (I) are administered by methods well known in the art, such as enteral, parenteral, dermal or nasal in the form of suitable preparations.
  • the administration can be prophylactic or therapeutic.
  • one embodiment of the present invention relates to the use of a compound of formula (I) as a medicament.
  • Another aspect relates to the use of a compound of formula (I) as an antiendoparasitic agent, in particular as a helminthicide or antiprotozoal agent.
  • Compounds of the formula (I) are suitable for use as antiendoparasitic agents, in particular as a helminthicide or antiprotozoal agents, for example in animal breeding, animal husbandry, in stables and in the hygiene sector.
  • a further aspect in turn relates to the use of a compound of the formula (I) as an antiectica, in particular an arthropodicide such as an insecticide or an acaricide.
  • Another aspect relates to the use of a compound of the formula (I) as anticancer drug, in particular an arthropodicide such as an insecticide or acaricide, for example in animal husbandry, in animal husbandry, in stables or in the hygiene sector.
  • a vector in the context of the present invention is an arthropod, in particular an insect or arachnid, which is able to attack pathogens such.
  • pathogens such as viruses, worms, protozoa and bacteria from a reservoir (plant, animal, human, etc.) to a host to transfer.
  • the pathogens may be transferred to a host either mechanically (e.g., trachoma by non-stabbing flies) on a host, or after injection (e.g., malaria parasites by mosquitoes).
  • vectors in the context of the present invention are insects such as aphids, flies, cicadas or thrips, which can transmit plant viruses to plants.
  • Other vectors that can transmit plant viruses are spider mites, lice, beetles and nematodes.
  • vectors for the purposes of the present invention are insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, for example A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and culex, lice, fleas, flies, mites and ticks that can transmit pathogens to animals and / or humans.
  • insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, for example A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and culex, lice, fleas, flies, mites and ticks that can transmit pathogens to animals and / or humans.
  • Vector control is also possible when the compounds of formula (I) are resistance-disrupting.
  • Compounds of formula (I) are suitable for use in the prevention of disease or pathogens transmitted by vectors.
  • another aspect of the present invention is the non-therapeutic use of compounds of formula (I) for vector control, e.g. in agriculture, horticulture, forests, gardens and recreational facilities, as well as in the protection of materials and materials.
  • the compounds of formula (I) are useful for protecting engineering materials against attack or destruction by insects, e.g. from the order Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera and Zygentoma.
  • the compounds of the formula (I) are used together with at least one further insecticide and / or at least one fungicide.
  • the compounds of formula (I) are present as a ready-to-use pest control agent, that is, it can be applied to the corresponding material without further changes.
  • insecticides or as fungicides in particular the above-mentioned in question are further insecticides or as fungicides in particular the above-mentioned in question.
  • the compounds of the formula (I) can be used to protect against the growth of objects, in particular hulls, sieves, nets, structures, quays and signal systems, which come into contact with seawater or brackish water.
  • the compounds of the formula (I) can be used alone or in combination with other active substances as antifouling agents.
  • the compounds of the formula (I) are suitable for controlling animal pests in the hygiene sector.
  • the invention can be used in household, hygiene and storage protection, especially for controlling insects, arachnids and mites, which occur in enclosed spaces, such as apartments, factories, offices, vehicle cabins.
  • the compounds of formula (I) are used alone or in combination with other active ingredients and / or adjuvants.
  • they are used in household insecticide products.
  • the compounds of formula (I) are active against sensitive and resistant species and against all stages of development.
  • pests of the class Arachnida from the orders Scorpiones, Araneae and Opiliones, from the classes Chilopoda and Diplopoda, from the class Insecta the order Blattodea, from the orders Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera, Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria or Orthoptera, Siphonaptera and Zygentoma and from the class Malacostraca the order Isopoda.
  • Application is for example in aerosols, non-pressurized sprays, e.g. Pump and atomizer sprays, misting machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller driven evaporators, energyless or passive evaporation systems, moth papers, moth cakes and moth gels, as granules or dusts, in litter or bait stations.
  • Pump and atomizer sprays misting machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller driven evaporators, energyless or passive evaporation systems, moth papers, moth cakes and moth gels, as granules or dusts, in litter or bait stations.
  • the calibration is carried out with unbranched alkan-2-ones (with 3 to 16 carbon atoms), whose logP values are known (determination of the logP values by means of the retention times by linear interpolation between two consecutive alkanones).
  • the NMR spectra were determined on a Bruker Avance 400 equipped with a flow-through head (60 ⁇ l volume). In individual cases the NMR spectra were measured with a Bruker Avance II 600.
  • the 1 H NMR data of selected examples are noted in terms of 1 H NMR peaks. For each signal peak, first the ⁇ -value in ppm and then the signal intensity in round brackets are listed. The ⁇ value - signal intensity number pairs of different signal peaks are listed separated by semicolons.
  • the peak list of an example therefore has the form: ⁇ 1 (intensity 1); ⁇ 2 (intensity 2); ........; ⁇ i (intensity i); ......; ⁇ n (intensity n)
  • the intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. For broad signals, multiple peaks or the center of the signal and their relative intensity can be shown compared to the most intense signal in the spectrum.
  • the peaks of stereoisomers of the target compounds and / or peaks of impurities usually have on average a lower intensity than the peaks of the target compounds (for example with a purity of> 90%).
  • Such stereoisomers and / or impurities may be typical of the particular preparation process. Their peaks can thus help identify the reproduction of our manufacturing process by "by-product fingerprints.”
  • An expert calculating the peaks of the target compounds by known methods can isolate the peaks of the target compounds as needed, using additional intensity filters if necessary. This isolation would be similar to peak-picking in classical 1 H NMR interpretation.
  • Step 1 N - (2,6-dichloro-3-pyridyl) pyridine-3-carboxamide
  • Step 1 N - [2-Chloro-6- (trifluoromethyl) -3-pyridyl] pyridine-3-carboxamide
  • N- [2-chloro-6- (trifluoromethyl) -3-pyridyl] pyridine-3-carboxamide was carried out in analogy to the synthesis of N - (2,6-dichloro-3-pyridyl) pyridine-3-carboxamide.
  • 2-chloro-6- (trifluoromethyl) pyridin-3-amine 200 mg, 1.02 mmol
  • pyridine-3-carboxylic acid chloride hydrochloride 543 mg, 3.05 mmol
  • pyridine (0, 66 mL, 8.1 mmol) in acetonitrile for 31 h at room temperature.
  • Step 2 2- (3-Pyridyl) -5- (trifluoromethyl) thiazolo [5,4-b] pyridine (Example 10)
  • Step 1 N - (2,6-Dibromopyridin-3-yl) nicotinamide
  • Step 3 Methyl 2- (pyridin-3-yl) [1,3] thiazolo [5,4-b] pyridine-5-carboxylate
  • Step 1 tert -Butyl [2- (pyridin-3-yl) [1,3] thiazolo [5,4-b] pyridin-5-yl] carbamate
  • Step 2 2- (Pyridin-3-yl) [1,3] thiazolo [5,4-b] pyridin-5-amine
  • the reaction mixture was rinsed several times with an argon stream and the vessel was closed.
  • the mixture was heated to 140 ° C in a CEM Discover microwave for 40 minutes and, after cooling to room temperature, filtered through a depth filter which was rinsed with ethyl acetate.
  • the reaction was carried out twice in total and the mixtures were combined before purification. After removing the solvent under reduced pressure, the residue was chromatographed on silica gel by MPLC (gradient: ethyl acetate / cyclohexane 0: 100 ⁇ 30:70).
  • Meta- chloroperbenzoic acid (70% pure, 33 mg, 0.14 mmol) was added to a solution of 6- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfanyl) phenyl] at 0 ° C.
  • 2- (3-pyridyl) thiazolo [5,4-b] pyridine 60 mg, 0.13 mmol
  • CH 2 Cl 2 2.5 mL
  • the reaction mixture was stirred for 2 h at room temperature and then treated with saturated sodium carbonate solution. After 15 minutes, the phases were separated, the aqueous phase extracted with CH 2 Cl 2 and the combined organic phases dried with sodium sulfate. The solvent was removed under reduced pressure.
  • 5-chloro-2- (3-pyridyl) thiazolo [5,4-b] pyridine 100 mg, 0.40 mmol
  • 4-methyl-3- (2,2,2-trifluoroethylsulfanyl) aniline 134 mg, 0.61 mmol
  • palladium (II) acetate 4.5 mg, 20 ⁇ mol
  • rac - (2,2'-bis (diphenylphosphino) -1,1'-binaphthyl) 5 mg, 8 ⁇ mol
  • sodium tert-butoxide 58 mg, 0.60 mmol
  • reaction mixture was freed from dissolved oxygen by introducing an argon stream for 20 minutes and then stirred at 110 ° C. for 16 hours. After cooling to room temperature, the mixture was filtered through a depth filter, which was then rinsed with ethyl acetate. The solvent was removed under reduced pressure and the residue was chromatographed on silica gel by MPLC (gradient: ethyl acetate / cyclohexane 0: 100 ⁇ 100: 0). Thus, 29 mg (100% purity, 24% yield) of 4- [2- (3-pyridyl) thiazolo [5,4-b] pyridin-5-yl] morpholine could be obtained.
  • Example 13 2- (3-Pyridyl) -5- [4- (trifluoromethyl) pyrazol-1-yl] thiazolo [5,4-b] pyridine
  • the vessel was capped and the reaction mixture heated in a CEM Discover microwave to 120 ° C for 18 h. After cooling to room temperature, ethyl acetate was added and the mixture was filtered through a depth filter, which was then rinsed with ethyl acetate. The solvent was removed under reduced pressure and the residue was chromatographed on silica gel by MPLC (gradient: ethyl acetate / cyclohexane 0: 100 ⁇ 50:50). Subsequently, again by HPLC (gradient: H 2 O / acetonitrile) was separated by chromatography.
  • Examples 1-4 are not included in the scope of protection and are to be regarded as comparative examples.
  • ⁇ b> ⁇ u> Table 2 ⁇ / u> ⁇ /b> Analytical data for the specified compounds.
  • Expl logP [a] logP [b] 1 H-NMR [ ⁇ (ppm)] or LC-MS [m / z] 1 4.81 4.75 1 H NMR (400.0 MHz, d 6 -DMSO): ⁇ 9.366 (9.6); 9,331 (9.4); 9,330 (9.2); 8.819 (7.7); 8.815 (8.5); 8,807 (8.3); 8.803 (8.5); 8,615 (14.3); 8,593 (16.0); 8,536 (4.4); 8.532 (5.7); 8,530 (5.6); 8,526 (4.5); 8,516 (4.8); 8,512 (5.8); 8.510 (6.2); 8,506 (4.6); 8,318 (0.8); 8,208 (9.7); 8,188 (9.7); 8,040 (6.9); 8,036 (7.9); 8,
  • Solvent 78 Parts by weight acetone 1.5 Parts by weight of dimethylformamide emulsifier: Alkylarylpolyglykolether
  • active compound 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water.
  • Chinese cabbage leaf discs Brassica pekinensis ) infested with all stages of the green peach aphid ( Myzus persicae ) are sprayed with an active compound preparation of the desired concentration.
  • Solvent 78.0 Parts by weight of acetone 1.5 Parts by weight of dimethylformamide emulsifier: Alkylarylpolyglykolether
  • active compound 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water.
  • Bean leaf discs Phaseolus vulgaris infected by all stages of the common spider mite (Tetranychus urticae) are sprayed with an active compound preparation of the desired concentration.
  • Solvent 7 parts by weight of dimethylformamide emulsifier: Alkylarylpolyglykolether
  • a suitable preparation of active compound 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration.
  • emulsifier concentration 1000 ppm until reaching the desired concentration.
  • dilute with emulsifier-containing water dilute with ammonium salts or / and penetration promoters they are added in each case in a concentration of 1000 ppm of the preparation solution.
  • Paprika plants Capsicum annuum ) which are heavily infested with the green peach aphid ( Myzus persicae ) are treated by spraying with the preparation of active compound in the desired concentration.
  • Solvent 7 parts by weight of dimethylformamide emulsifier: Alkylarylpolyglykolether
  • a suitable preparation of active compound 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration.
  • emulsifier concentration 1000 ppm until reaching the desired concentration.
  • dilute with emulsifier-containing water dilute with ammonium salts or / and penetration promoters they are added in each case in a concentration of 1000 ppm of the preparation solution.
  • Cotton plants which are heavily attacked by the cotton aphid ( Aphis gossypii ) are sprayed with an active compound preparation of the desired concentration.
  • the kill is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.

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Description

Die vorliegende Anmeldung betrifft neue bicyclische Verbindungen, Mittel enthaltend diese Verbindungen, ihre Verwendung zur Bekämpfung von tierischen Schädlingen sowie Verfahren und Zwischenprodukte zu Ihrer Herstellung.The present application relates to novel bicyclic compounds, agents containing these compounds, their use for combating animal pests and methods and intermediates for their preparation.

Kürzlich sind bicyclische Verbindungen bekannt geworden, die insektizide Eigenschaften besitzen ( WO 2015/038503 A1 ).Recently, bicyclic compounds have become known which possess insecticidal properties ( WO 2015/038503 A1 ).

In WO 2010/051196 und WO 2009/155017 sind Aryl oder Heteroaryl substituierte Azabenzoxazole und Azabenzthiazole für pharmazeutische und diagnostische Anwendungen beschrieben.In WO 2010/051196 and WO 2009/155017 Aryl or heteroaryl substituted azabenzoxazoles and azabenzothiazoles are described for pharmaceutical and diagnostic applications.

In US 4,038,396 wird über die Synthese verschiedener Thiazolo[5,4-b]pyridine und Oxazolo[5,4-b]pyridine für pharmazeutische Anwendungen berichtet. WO2012/136751 offenbart Thiazolo[5,4b]pyridin-Bizyklen zur Bekämpfung von Schädlingen.In US 4,038,396 is reported on the synthesis of various thiazolo [5,4-b] pyridines and oxazolo [5,4-b] pyridines for pharmaceutical applications. WO2012 / 136751 discloses thiazolo [5,4b] pyridine cyclic pest control cycles.

Moderne Pflanzenschutzmittel müssen vielen Anforderungen genügen, beispielsweise in Bezug auf Höhe, Dauer und Breite ihrer Wirkung und möglichen Verwendung. Es spielen Fragen der Toxizität, der Kombinierbarkeit mit anderen Wirkstoffen oder Formulierhilfsmitteln eine Rolle sowie die Frage des Aufwands, der für die Synthese eines Wirkstoffs betrieben werden muss. Ferner können Resistenzen auftreten. Schon aus all diesen Gründen kann die Suche nach neuen Pflanzenschutzmitteln nicht als abgeschlossen betrachtet werden und es besteht ständig Bedarf an neuen Verbindungen mit gegenüber den bekannten Verbindungen zumindest in Bezug auf einzelne Aspekte verbesserten Eigenschaften. Aufgabe der vorliegenden Erfindung war es, Verbindungen bereitzustellen, durch die das Spektrum der Schädlingsbekämpfungsmittel unter verschiedenen Aspekten verbreitert wird.Modern plant protection products have to meet many requirements, for example with regard to the amount, duration and breadth of their effect and possible use. Issues of toxicity, of the ability to be combined with other active substances or formulation auxiliaries play a role, as well as the question of the effort that has to be spent on the synthesis of an active substance. Furthermore, resistances can occur. For all these reasons, the search for new pesticides can not be considered complete and there is a constant need for new compounds with improved properties compared with the known compounds, at least with regard to individual aspects. The object of the present invention was to provide compounds which broaden the spectrum of pesticides from various aspects.

Gelöst wird die Aufgabe, sowie weitere nicht explizit genannte Aufgaben, die aus den hierin diskutierten Zusammenhängen ableitbar oder erschließbar sind, durch neue Verbindungen der Formel (I)

Figure imgb0001
in welcher

A
für einen A-Rest aus der Reihe (A-b) bis (A-f)
Figure imgb0002
 worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet und
B2
für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Nitro, Alkyl, Halogenalkyl, Alkoxy, Halogenalkoxy und jeweils gegebenenfalls substituiertes Cycloalkyl und Cycloalkenyl steht,
Q
für Sauerstoff oder Schwefel steht,
R1
für einen Rest aus der Reihe Wasserstoff, Alkyl, Alkoxy und Cyano steht,
R2
a) für einen B-Rest aus der Reihe
Figure imgb0003
Figure imgb0004
Figure imgb0005
Figure imgb0006
Figure imgb0007
Figure imgb0008
Figure imgb0009
Figure imgb0010
Figure imgb0011
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder
R2
b) für einen D-Rest aus der Reihe (D-1) bis (D-3)
Figure imgb0012
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder
R2
c) für einen Rest der Formel
Figure imgb0013
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder
R2
d) für einen Rest der Formel
Figure imgb0014
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder
R2
e) für einen F-Rest aus der Reihe (F-1) bis (F-11)
Figure imgb0015
Figure imgb0016
Figure imgb0017
Figure imgb0018
 steht,
worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder
R2
f) für einen Rest aus der Reihe Halogenalkyl und Carboxyl steht,
R2
g) für einen Rest der Formel
Figure imgb0019
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet,
worin
G2
für Wasserstoff oder einen Rest aus der Reihe Halogen, Nitro, Amino, Cyano, Alkylamino, Halogenalkylamino, Dialkylamino, Alkyl, Halogenalkyl, gegebenenfalls substituiertes und gegebenenfalls durch ein oder mehrere Heteroatome unterbrochenes gesättigtes oder ungesättigtes Cycloalkyl, Cycloalkylalkyl, Alkoxy, Halogenalkoxy, Alkoxyalkyl, halogeniertes Alkoxyalkyl, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl, Bis(alkoxy)alkyl, Bis(halogenalkoxy)alkyl, Alkoxy(alkylsulfanyl)alkyl, Alkoxy(alkylsulfinyl)alkyl, Alkoxy(alkylsulfonyl)alkyl, Bis(alkylsulfanyl)alkyl, Bis(halogenalkylsulfanyl)alkyl, Bis(hydroxyalkylsulfanyl)alkyl, Alkoxycarbonyl, Alkoxycarbonylalkyl, alpha-Hydroxyiminoalkoxycarbonylalkyl, alpha-Alkoxyimino-alkoxycarbonylalkyl, C(X2)NR3R4, NR6R7, Alkylthio, Alkylsulfinyl, Alkylsulfonyl, Halogenalkylthio, Halogenalkylsulfinyl, Halogenalkylsulfonyl, die Heterocyclylreste Dioxanyl, Dioxolanyl, Dioxepanyl, Dioxocanyl, Oxathianyl, Oxathiolanyl, Oxathiepanyl, Oxathiocanyl, Dithianyl, Dithiolanyl, Dithiepanyl, Dithiocanyl, Oxathianyloxid, Oxathiolanyloxid, Oxathiepanyloxid, Oxathiocanyloxid, Oxathianyldioxid, Oxathiolanyldioxid, Oxathiepanyldioxid, Oxathiocanyldioxid, Morpholinyl, Triazolinonyl, Oxazolinyl, Dihydrooxadiazinyl, Dihydrodioxazinyl, Dihydrooxazolyl, Dihydrooxazinyl und Pyrazolinonyl (welche selbst wiederum substituiert sein können durch Alkyl, Halogenalkyl, Alkoxy und Alkoxyalkyl), Phenyl (welches selbst wiederum substituiert sein kann durch Halogen, Cyano, Nitro, Alkyl und Halogenalkyl), die Heteroarylreste Pyridyl, Pyridyl-N-oxid, Pyrimidyl, Imidazolyl, Pyrazolyl, Oxazolyl, Thiazolyl, Furanyl, Thienyl, Triazolyl, Tetrazolyl, Oxadiazolyl, Thiadiazolyl, Pyrazinyl, Triazinyl, Tetrazinyl und Isochinolinyl (welche selbst wiederum substituiert sein können durch Halogen, Nitro, Alkyl, Halogenalkyl, Alkoxy, Halogenalkoxy, Alkoxyalkyl, Alkylthio, Alkylthioalkyl und Cycloalkyl) und die Heteroarylalkylreste Triazolylalkyl, Pyridylalkyl, Pyrimidylalkyl und Oxadiazolylalkyl (welche selbst wiederum substituiert sein können durch Halogen und Alkyl) steht,
oder
G2
für einen C-Rest aus der Reihe (C-1) bis (C-9)
Figure imgb0020
Figure imgb0021
Figure imgb0022
 worin die gestrichelte Linie die Bindung zu den B-Resten bedeutet,
X
für Sauerstoff oder Schwefel steht,
X
für Sauerstoff oder Schwefel steht,
X1
für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Nitro, Alkyl, Halogenalkyl, Cycloalkyl, Alkoxy und Halogenalkoxy steht,
X2
für Sauerstoff, Schwefel, NR5 oder NOH steht,
L
für Sauerstoff oder Schwefel steht,
V-Z
für R24CH-CHR25 oder R24C=CR25 steht,
n
für 1 oder 2 steht,
m
für 1, 2, 3 oder 4 steht,
R
für NR18R19 oder für einen jeweils gegebenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Alkoxyalkyl, Alkyl-S-alkyl, Alkyl-S(O)-alkyl, Alkyl-S(O)2-alkyl, R18-CO-alkyl, NR18R19-CO-alkyl, Cycloalkyl, Cycloalkenyl, Cycloalkylalkyl, Cycloalkenylalkyl, Heterocyclyl, Heterocyclylalkyl, Phenyl, Phenylalkyl, Hetaryl und Hetarylalkyl steht,
R3
für Wasserstoff oder Alkyl steht,
R4
für einen Rest aus der Reihe Wasserstoff, Alkyl, Halogenalkyl, Cyanoalkyl, Alkinyl, Cycloalkyl, Cycloalkylalkyl, Alkoxyalkyl, Alkoxycarbonyl, Alkoxycarbonylalkyl, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl, Aryl, Arylalkyl und Hetarylalkyl steht,
R5
für einen Rest aus der Reihe Wasserstoff, Alkyl, Halogenalkyl, Cyanoalkyl, Alkinyl, Cycloalkyl, Cycloalkylalkyl, Alkoxyalkyl, Alkoxycarbonyl, Alkoxycarbonylalkyl, Alkylthioalkyl, Aryl, Arylalkyl und Hetarylalkyl steht, oder
R3 und R4
gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen Ring bilden, der ein oder mehrere weitere Heteroatome aus der Reihe Stickstoff, Sauerstoff und Schwefel enthalten kann, oder
R3 und R5
gemeinsam mit den Stickstoffatomen, an die sie gebunden sind, einen Ring bilden,
R6
für Wasserstoff oder Alkyl steht,
R7
für einen Rest aus der Reihe Wasserstoff, Alkyl, Halogenalkyl, Cyanoalkyl, Alkinyl, Cycloalkyl, Cycloalkylalkyl, Alkoxy, Halogenalkoxy, Alkoxyalkyl, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl, Alkoxycarbonyl, Alkoxycarbonylalkyl, Alkylthioalkyl, Aryl, Arylalkyl oder Hetarylalkyl steht, oder
R6 und R7
gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen Ring bilden, der ein oder mehrere weitere Heteroatome aus der Reihe Stickstoff, Sauerstoff und Schwefel enthalten kann,
R8
für einen Rest aus der Reihe Wasserstoff, Alkyl, Halogenalkyl, Cyanoalkyl, Alkoxy, Halogenalkoxy, Alkenyl, Alkoxyalkyl, jeweils gegebenenfalls durch Halogen substituiertes Alkylcarbonyl und Alkylsulfonyl, gegebenenfalls durch Halogen substituiertes Alkoxycarbonyl, gegebenenfalls durch Halogen, Alkyl, Alkoxy, Halogenalkyl und Cyano substituiertes Cycloalkylcarbonyl steht, oder für ein Kation oder ein gegebenenfalls durch Alkyl oder Arylalkyl substituiertes Ammonium-Ion steht,
R9
für einen Rest aus der Reihe jeweils gegebenenfalls substituiertes Alkyl, Alkenyl und Alkinyl, jeweils gegebenenfalls substituiertes Cycloalkyl, Cycloalkylalkyl und Cycloalkenyl, in welchen die Ringe mindestens ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff enthalten können, jeweils gegebenenfalls substituiertes Aryl, Heteroaryl, Arylalkyl und Heteroarylalkyl und eine gegebenenfalls substituierte Aminogruppe steht,
R8 und R9
in den Resten (C-1) und (F-1) auch zusammen mit der N-S(O)n-Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring bilden können, der ein oder mehrere weitere Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann,
R10
für Wasserstoff oder Alkyl steht,
R8 und R10
in den Resten (C-2) und (F-2) auch gemeinsam mit den N-Atomen an die sie gebunden sind, für einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring stehen können, der mindestens ein weiteres Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann,
R9 und R10
in den Resten (C-2) und (F-2) auch zusammen mit der N-S(O)n Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring bilden können, der ein oder mehrere weitere Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann,
R11
für einen jeweils gegebenenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Alkoxy, Alkenyloxy, Alkinyloxy, Cycloalkyl, Cycloalkyloxy, Cycloalkenyloxy, Cycloalkylalkoxy, Alkylthio, Alkenylthio, Phenoxy, Phenylthio, Benzyloxy, Benzylthio, Heteroaryloxy, Heteroarylthio, Heteroarylalkoxy und Heteroarylalkylthio steht,
R12
für einen jeweils gegebenenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Alkoxy, Alkenyloxy, Alkinyloxy, Cycloalkyl, Cycloalkyloxy, Cycloalkenyloxy, Cycloalkylalkoxy, Alkylthio, Alkenylthio, Phenoxy, Phenylthio, Benzyloxy, Benzylthio, Heteroaryloxy, Heteroarylthio, Heteroarylalkoxy und Heteroarylalkylthio steht,
R11 und R12
in den Resten (C-3) und (F-3) auch gemeinsam mit dem Phosphoratom, an das sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 5- bis 7-gliedrigen Ring bilden können, der ein oder zwei Heteroatome aus der Reihe Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Schwefel enthalten kann,
R13
für einen jeweils gegebenenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Phenyl und Phenylalkyl steht,
R14
für einen jeweils gegebenenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Phenyl und Phenylalkyl steht,
R15
für einen Rest aus der Reihe jeweils gegebenenfalls substituiertes Alkyl, Alkenyl und Alkinyl, jeweils gegebenenfalls substituiertes Cycloalkyl, Cycloalkylalkyl und Cycloalkenyl, in welchen die Ringe mindestens ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff enthalten können, jeweils gegebenenfalls substituiertes Aryl, Heteroaryl, Arylalkyl und Heteroarylalkyl und eine gegebenenfalls substituierte Aminogruppe steht,
R8 und R15
in den Resten (C-6) und (F-6) auch zusammen mit der N-S(O)n Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring bilden können, der ein oder mehrere weitere Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann,
R16
für einen Rest aus der Reihe Wasserstoff, jeweils gegebenenfalls substituiertes Alkyl, Alkoxy, Alkenyl und Alkinyl, jeweils gegebenenfalls substituiertes Cycloalkyl, Cycloalkylalkyl und Cycloalkenyl, in welchen die Ringe mindestens ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff enthalten können, jeweils gegebenenfalls substituiertes Aryl, Heteroaryl, Arylalkyl und Heteroarylalkyl und eine gegebenenfalls substituierte Aminogruppe steht,
R8 und R16
in den Resten (C-7) und (F-7) auch zusammen mit dem N-Atom, an das sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring bilden können, der ein oder mehrere weitere Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann,
R17
für einen Rest aus der Reihe jeweils gegebenenfalls substituiertes Alkyl, Alkoxy, Alkenyl und Alkinyl, jeweils gegebenenfalls substituiertes Cycloalkyl, Cycloalkylalkyl und Cycloalkenyl, in welchen die Ringe mindestens ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff enthalten können, jeweils gegebenenfalls substituiertes Aryl, Heteroaryl, Arylalkyl und Heteroarylalkyl und eine gegebenenfalls substituierte Aminogruppe steht,
R8 und R17
in den Resten (C-8) und (F-8) auch zusammen mit der N-C(X) Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring bilden können, der ein oder mehrere weitere Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann,
R18
für einen Rest aus der Reihe Wasserstoff, Hydroxy, jeweils gegebenenfalls substituiertes Alkyl, Alkoxy, Alkoxyalkyl, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl, Alkylcarbonyl, Alkoxycarbonyl, Alkenyl und Alkinyl, jeweils gegebenenfalls substituiertes Cycloalkyl, Cycloalkylalkyl, Cycloalkenyl und Cycloalkenylalkyl, in welchen die Ringe mindestens ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff enthalten können, jeweils gegebenenfalls substituiertes Aryl, Arylalkyl, Heteroaryl und Heteroarylalkyl und eine gegebenenfalls substituierte Aminogruppe steht,
R19
für einen Rest aus der Reihe Wasserstoff, für ein Alkali- oder Erdalkalimetallion oder für ein gegebenfalls einfach bis vierfach durch C1-C4-Alkyl substituiertes Ammoniumion oder für einen jeweils gegebenenfalls durch Halogen oder Cyano substituierten Rest aus der Reihe Alkyl, Alkoxy, Alkoxyalkyl, Alkylthioalkyl, Alkylsulfinylalkyl und Alkylsulfonylalkyl steht,
Y1 und Y2
unabhängig voneinander für C=O oder S(O)2 stehen,
Y3
für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Alkyl, Cycloalkyl, Halogenalkyl, Alkoxy, Halogenalkoxy und NR20R21 steht,
W
für einen Rest aus der Reihe O, S, SO und SO2 steht,
R22
für einen Rest aus der Reihe Wasserstoff, Alkyl, Halogenalkyl, Cyanoalkyl, Alkenyl, Halogenalkenyl, Alkinyl, Halogenalkinyl, Alkoxy, Halogenalkoxy, gegebenenfalls durch Halogen substituiertes Alkoxyalkyl, gegebenenfalls durch Halogen substituiertes Bis(alkoxy)alkyl, gegebenenfalls durch Halogen substituiertes Alkylsulfanylalkyl, gegebenenfalls durch Halogen substituiertes Alkylcarbonylalkyl, gegebenenfalls durch Halogen substituiertes Alkylsulfinylalkyl, gegebenenfalls durch Halogen substituiertes Alkylsulfonylalkyl, Dialkylaminosulfanylalkyl, Dialkylaminosulfinylalkyl, Dialkylaminosulfonylalkyl, gegebenenfalls durch Halogen substituiertes Alkoxycarbonyl, gegebenenfalls durch Halogen substituiertes Alkoxycarbonylalkyl, gegebenenfalls durch Halogen substituiertes Alkinyloxy, gegebenenfalls durch Halogen substituiertes Alkinyloxycarbonyl, Dialkylaminocarbonyl, N-Alkyl-N-Cycloalkylaminocarbonyl, Dialkylaminocarbonylalkyl, N-Alkyl-N-Cycloalkylaminocarbonylalkyl, Heterocyclyl-carbonylalkyl, Alkylsulfanyl, Halogenalkylsulfanyl, Alkylsulfinyl, Halogenalkylsulfinyl, Alkylsulfonyl, Halogenalkylsulfonyl, gegebenenfalls durch Halogen, Cyano, Nitro, Alkyl, Cycloalkyl, Halogenalkyl, Alkoxy, Halogenalkoxy, Alkoxycarbonyl, Halogenalkoxycarbonyl oder Hetaryl (welches gegebenenfalls selbst durch Alkyl oder Halogen substituiert ist) substituiertes Cycloalkyl, gegebenenfalls durch Halogen, Cyano, Nitro, Alkyl, Halogenalkyl, Cycloalkyl, Alkoxy, Halogenalkoxy, Alkoxycarbonyl, Halogenalkoxycarbonyl oder Hetaryl (welches gegebenenfalls selbst durch Alkyl oder Halogen substituiert ist) substituiertes Cycloalkylcarbonyl, gegebenenfalls durch Halogen, Cyano, Nitro, Alkyl, Halogenalkyl, Cycloalkyl, Alkoxy, Halogenalkoxy, Alkoxycarbonyl, Halogenalkoxycarbonyl oder Hetaryl (welches gegebenenfalls selbst durch Alkyl oder Halogen substituiert ist) substituiertes Cycloalkylalkyl, gegebenenfalls substituiertes Heterocyclyl, gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, Hydroxy, Alkyl, Halogenalkyl, Cycloalkyl (welches gegebenenfalls substituiert ist), Alkoxy, Halogenalkoxy, Alkylthio, Halogenalkylthio, Alkylsulfinyl, Alkylsulfonyl, Halogenalkylsulfinyl, Halogenalkylsulfonyl, Amino, Alkylamino, Dialkylamino, Alkylcarbonylamino, Alkoxycarbonylamino, Alkoxyalkyl, Halogenalkoxyalkyl, Alkenyl, Alkinyl, Cycloalkylalkyl, Alkylcarbonyl, Alkoxycarbonyl oder Aminocarbonyl substituiertes Heterocyclylalkyl, gegebenenfalls durch Halogen, Cyano, Nitro, Hydroxy, Amino, Alkyl, Halogenalkyl, Cycloalkyl (welches gegebenenfalls substituiert ist)Alkoxy oder Halogenalkoxy substituiertes Aryl, gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, Hydroxy, Amino, Alkyl, Cycloalkyl (welches gegebenenfalls substituiert ist), Halogenalkyl, Alkoxy oder Halogenalkoxy substituiertes Arylalkyl, gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, Hydroxy, Alkyl, Halogenalkyl, Cycloalkyl (welches gegebenenfalls substituiert ist), Alkoxy, Halogenalkoxy, Alkylthio, Halogenalkylthio, Alkylsulfinyl, Alkylsulfonyl, Halogenalkylsulfinyl, Halogenalkylsulfonyl, Amino, Alkylamino, Dialkylamino, Alkylcarbonylamino, Alkoxycarbonylamino, Alkoxyalkyl, Halogenalkoxyalkyl, Alkenyl, Alkinyl, Cycloalkylalkyl, Alkylcarbonyl, Alkoxycarbonyl oder Aminocarbonyl substituiertes Hetarylalkyl steht, oder
R22
für einen D-Rest aus der Reihe (D-1) bis (D-3)
Figure imgb0023
 einen E-Rest aus der Reihe (E-1) bis (E-11)
Figure imgb0024
Figure imgb0025
Figure imgb0026
 der Reihe (E-18) bis (E-51)
Figure imgb0027
Figure imgb0028
Figure imgb0029
Figure imgb0030
Figure imgb0031
Figure imgb0032
Figure imgb0033
Figure imgb0034
Figure imgb0035
Figure imgb0036
 steht, oder
im Fall R2 = d),
R22
auch für einen E-Rest aus der Reihe E-12 bis E-17
Figure imgb0037
Figure imgb0038
 steht, worin hier und später die gestrichelte Linie die Bindung zum entsprechenden Atom in den Resten c), d) und g) bedeutet,
R20
für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Nitro, Amino, Hydroxy und jeweils gegebenenfalls substituiertes Alkyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkylalkyl, Alkoxy, Alkenyloxy, Alkinyloxy, Cycloalkyloxy, Alkylcarbonyloxy, Alkenylcarbonyloxy, Alkinylcarbonyloxy, Cycloalkylcarbonyloxy, Alkoxycarbonyloxy, Alkylsulfonyloxy, Alkylamino, Alkenylamino, Alkinylamino, Cycloalkylamino, Alkylthio, Halogenalkylthio, Alkenylthio, Alkinylthio, Cycloalkylthio, Alkylsulfinyl, Alkylsulfonyl, Alkylcarbonyl, Alkoxyiminoalkyl, Alkoxycarbonyl, Aminocarbonyl, Alkylaminocarbonyl, Dialkylaminocarbonyl, Aminothiocarbonyl, Alkylaminosulfonyl, Alkylsulfonylamino, Alkylcarbonylamino, Alkenylcarbonylamino, Alkinylcarbonylamino, Cycloalkylcarbonylamino, Alkoxycarbonylamino, Alkylthiocarbonylamino, Bicycloalkyl, Aryl, Aryloxy, Heteroaryl und Heteroaryloxy steht, wobei die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Cyano, Nitro, Hydroxy, Amino, Alkyl und Halogenalkyl,
R21
für einen Rest aus der Reihe Wasserstoff, Alkyl, Cycloalkyl, Halogenalkyl, Alkenyl, Alkinyl, Cycloalkylalkyl, Cyanoalkyl, Alkylcarbonyl, Alkenylcarbonyl, Halogenalkylcarbonyl, Halogenalkenylcarbonyl, Alkoxyalkyl, Alkoxycarbonyl, Alkylsulfonyl und Halogenalkylsulfonyl steht,
R23
für einen Rest aus der Reihe Wasserstoff, Alkyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkenyl, Alkoxy, Alkenyloxy, Alkinyloxy, Cycloalkyloxy, Alkylthioalkyl, Alkenylthioalkyl, Cyanoalkyl, Alkoxyalkyl steht,
oder, für R2 = c) oder g),
R22 und R23
gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen Ring bilden, der ein oder mehrere weitere Heteroatome aus der Reihe Stickstoff, Sauerstoff und Schwefel enthalten kann, und
R24
für Wasserstoff oder einen jeweils gegebenenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Phenyl und Phenylalkyl steht und
R25
für Wasserstoff oder einen jeweils gegebenenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Phenyl und Phenylalkyl steht,
R26
für einen Rest aus der Reihe Wasserstoff, Alkyl, Halogenalkyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkylalkyl, Alkoxy-alkyl, Alkylsulfanyl, Halogenalkylsulfanyl, Alkylsulfinyl, Halogenalkylsulfinyl, Alkylsulfonyl, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl und Cyanoalkyl steht.
R27
für Wasserstoff, Alkyl, Halogenalkyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkylalkyl, Alkoxyalkyl, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl oder Cyanoalkyl steht und
Verbindungen der Formel (I), in welcher
A
für den A-Rest
Figure imgb0039
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet und
G1
für N oder C-B1 steht,
B1
für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Nitro, Alkyl, Halogenalkyl, Alkoxy, Halogenalkoxy und jeweils gegebenenfalls substituiertes Cycloalkyl und Cycloalkenyl steht,
B2
für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Nitro, Alkyl, Halogenalkyl, Alkoxy, Halogenalkoxy und jeweils gegebenenfalls substituiertes Cycloalkyl und Cycloalkenyl steht,
T
für Sauerstoff oder ein Elektronenpaar steht,
Q
für Sauerstoff oder Schwefel steht,
R1
für einen Rest aus der Reihe Wasserstoff, Alkyl, Alkoxy und Cyano steht,
R2
a) für einen B-Rest aus der Reihe
Figure imgb0040
Figure imgb0041
Figure imgb0042
Figure imgb0043
Figure imgb0044
Figure imgb0045
Figure imgb0046
Figure imgb0047
Figure imgb0048
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) markiert, oder
R2
c) für einen Rest der Formel
Figure imgb0049
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder
R2
d) für einen Rest der Formel
Figure imgb0050
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder
R2
e) für einen F-Rest aus der Reihe
Figure imgb0051
Figure imgb0052
Figure imgb0053
Figure imgb0054
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder
R2
f) für einen Rest aus der Reihe Halogenalkyl und Carboxyl steht,
R2
g) für einen Rest der Formel
Figure imgb0055
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, worin
G2
für Wasserstoff oder einen Rest aus der Reihe Halogen, Nitro, Amino, Cyano, Alkylamino, Halogenalkylamino, Dialkylamino, Alkyl, Halogenalkyl, gegebenenfalls substituiertes und gegebenenfalls durch ein oder mehrere Heteroatome unterbrochenes gesättigtes oder ungesättigtes Cycloalkyl, Cycloalkylalkyl, Alkoxy, Halogenalkoxy, Alkoxyalkyl, halogeniertes Alkoxyalkyl, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl, Bis(alkoxy)alkyl, Bis(halogenalkoxy)alkyl, Alkoxy(alkylsulfanyl)alkyl, Alkoxy(alkylsulfinyl)alkyl, Alkoxy(alkylsulfonyl)alkyl, Bis(alkylsulfanyl)alkyl, Bis(halogenalkylsulfanyl)alkyl, Bis(hydroxyalkylsulfanyl)alkyl, Alkoxycarbonyl, Alkoxycarbonylalkyl, alpha-Hydroxyiminoalkoxycarbonylalkyl, alpha-Alkoxyimino-alkoxycarbonylalkyl, C(X2)NR3R4, NR6R7, Alkylthio, Alkylsulfinyl, Alkylsulfonyl, Halogenalkylthio, Halogenalkylsulfinyl, Halogenalkylsulfonyl, die Heterocyclylreste Dioxanyl, Dioxolanyl, Dioxepanyl, Dioxocanyl, Oxathianyl, Oxathiolanyl, Oxathiepanyl, Oxathiocanyl, Dithianyl, Dithiolanyl, Dithiepanyl, Dithiocanyl, Oxathianyloxid, Oxathiolanyloxid, Oxathiepanyloxid, Oxathiocanyloxid, Oxathianyldioxid, Oxathiolanyldioxid, Oxathiepanyldioxid, Oxathiocanyldioxid, Morpholinyl, Triazolinonyl, Oxazolinyl, Dihydrooxadiazinyl, Dihydrodioxazinyl, Dihydrooxazolyl, Dihydrooxazinyl und Pyrazolinonyl (welche selbst wiederum substituiert sein können durch Alkyl, Halogenalkyl, Alkoxy und Alkoxyalkyl), Phenyl (welches selbst wiederum substituiert sein kann durch Halogen, Cyano, Nitro, Alkyl und Halogenalkyl), die Heteroarylreste Pyridyl, Pyridyl-N-oxid, Pyrimidyl, Imidazolyl, Pyrazolyl, Oxazolyl, Thiazolyl, Furanyl, Thienyl, Triazolyl, Tetrazolyl, Oxadiazolyl, Thiadiazolyl, Pyrazinyl, Triazinyl, Tetrazinyl und Isochinolinyl (welche selbst wiederum substituiert sein können durch Halogen, Nitro, Alkyl, Halogenalkyl, Alkoxy, Halogenalkoxy, Alkoxyalkyl, Alkylthio, Alkylthioalkyl und Cycloalkyl) und die Heteroarylalkylreste Triazolylalkyl, Pyridylalkyl, Pyrimidylalkyl und Oxadiazolylalkyl (welche selbst wiederum substituiert sein können durch Halogen und Alkyl) steht, oder
G2
für einen C-Rest aus der Reihe (C-1) bis (C-9)
Figure imgb0056
Figure imgb0057
Figure imgb0058
 steht, worin die gestrichelte Linie die Bindung zu den B-Resten bedeutet,
X
für Sauerstoff oder Schwefel steht,
X2
für Sauerstoff, Schwefel, NR5 oder NOH steht,
L
für Sauerstoff oder Schwefel steht,
V-Z
für R24CH-CHR25 oder R24C=CR25 steht,
n
für 1 oder 2 steht,
m
für 1, 2, 3 oder 4 steht,
R3
für Wasserstoff oder Alkyl steht,
R4
für einen Rest aus der Reihe Wasserstoff, Alkyl, Halogenalkyl, Cyanoalkyl, Alkinyl, Cycloalkyl, Cycloalkylalkyl, Alkoxyalkyl, Alkoxycarbonyl, Alkoxycarbonylalkyl, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl, Aryl, Arylalkyl und Hetarylalkyl steht,
R5
für einen Rest aus der Reihe Wasserstoff, Alkyl, Halogenalkyl, Cyanoalkyl, Alkinyl, Cycloalkyl, Cycloalkylalkyl, Alkoxyalkyl, Alkoxycarbonyl, Alkoxycarbonylalkyl, Alkylthioalkyl, Aryl, Arylalkyl und Hetarylalkyl steht, oder
R3 und R4
gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen Ring bilden, der ein oder mehrere weitere Heteroatome aus der Reihe Stickstoff, Sauerstoff und Schwefel enthalten kann, oder
R3 und R5
gemeinsam mit den Stickstoffatomen, an die sie gebunden sind, einen Ring bilden,
R6
für Wasserstoff oder Alkyl steht,
R7
für einen Rest aus der Reihe Wasserstoff, Alkyl, Halogenalkyl, Cyanoalkyl, Alkinyl, Cycloalkyl, Cycloalkylalkyl, Alkoxy, Halogenalkoxy, Alkoxyalkyl, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl, Alkoxycarbonyl, Alkoxycarbonylalkyl, Alkylthioalkyl, Aryl, Arylalkyl oder Hetarylalkyl steht, oder
R6 und R7
gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen Ring bilden, der ein oder mehrere weitere Heteroatome aus der Reihe Stickstoff, Sauerstoff und Schwefel enthalten kann,
R8
für einen Rest aus der Reihe Wasserstoff, Alkyl, Halogenalkyl, Cyanoalkyl, Alkoxy, Halogenalkoxy, Alkenyl, Alkoxyalkyl, jeweils gegebenenfalls durch Halogen substituiertes Alkylcarbonyl und Alkylsulfonyl, gegebenenfalls durch Halogen substituiertes Alkoxycarbonyl, gegebenenfalls durch Halogen, Alkyl, Alkoxy, Halogenalkyl und Cyano substituiertes Cycloalkylcarbonyl steht, oder für ein Kation oder ein gegebenenfalls durch Alkyl oder Arylalkyl substituiertes Ammonium-Ion steht,
R9
für einen Rest aus der Reihe jeweils gegebenenfalls substituiertes Alkyl, Alkenyl und Alkinyl, jeweils gegebenenfalls substituiertes Cycloalkyl, Cycloalkylalkyl und Cycloalkenyl, in welchen die Ringe mindestens ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff enthalten können, jeweils gegebenenfalls substituiertes Aryl, Heteroaryl, Arylalkyl und Heteroarylalkyl und eine gegebenenfalls substituierte Aminogruppe steht,
R8 und R9
im Rest (C-1) auch zusammen mit der N-S(O)n-Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring bilden können, der ein oder mehrere weitere Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann,
R10
für Wasserstoff oder Alkyl steht,
R8 und R10
in den Resten (C-2) und (F-2) auch gemeinsam mit den N-Atomen an die sie gebunden sind, für einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring stehen können, der mindestens ein weiteres Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann,
R9 und R10
in den Resten (C-2) und (F-2) auch zusammen mit der N-S(O)n Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring bilden können, der ein oder mehrere weitere Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann,
R11
für einen jeweils gegebenenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Alkoxy, Alkenyloxy, Alkinyloxy, Cycloalkyl, Cycloalkyloxy, Cycloalkenyloxy, Cycloalkylalkoxy, Alkylthio, Alkenylthio, Phenoxy, Phenylthio, Benzyloxy, Benzylthio, Heteroaryloxy, Heteroarylthio, Heteroarylalkoxy und Heteroarylalkylthio steht,
R12
für einen jeweils gegebenenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Alkoxy, Alkenyloxy, Alkinyloxy, Cycloalkyl, Cycloalkyloxy, Cycloalkenyloxy, Cycloalkylalkoxy, Alkylthio, Alkenylthio, Phenoxy, Phenylthio, Benzyloxy, Benzylthio, Heteroaryloxy, Heteroarylthio, Heteroarylalkoxy und Heteroarylalkylthio steht,
R11 und R12
in den Resten (C-3) und (F-3) auch gemeinsam mit dem Phosphoratom, an das sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 5- bis 7-gliedrigen Ring bilden können, der ein oder zwei Heteroatome aus der Reihe Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Schwefel enthalten kann,
R13
für einen jeweils gegebenenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Phenyl und Phenylalkyl steht,
R14
für einen jeweils gegebenenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Phenyl und Phenylalkyl steht,
R15
für einen Rest aus der Reihe jeweils gegebenenfalls substituiertes Alkyl, Alkenyl und Alkinyl, jeweils gegebenenfalls substituiertes Cycloalkyl, Cycloalkylalkyl und Cycloalkenyl, in welchen die Ringe mindestens ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff enthalten können, jeweils gegebenenfalls substituiertes Aryl, Heteroaryl, Arylalkyl und Heteroarylalkyl und eine gegebenenfalls substituierte Aminogruppe steht,
R8 und R15
in den Resten (C-6) und (F-6) auch zusammen mit der N-S(O)n Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring bilden können, der ein oder mehrere weitere Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann,
R16
für einen Rest aus der Reihe Wasserstoff, jeweils gegebenenfalls substituiertes Alkyl, Alkoxy, Alkenyl und Alkinyl, jeweils gegebenenfalls substituiertes Cycloalkyl, Cycloalkylalkyl und Cycloalkenyl, in welchen die Ringe mindestens ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff enthalten können, jeweils gegebenenfalls substituiertes Aryl, Heteroaryl, Arylalkyl und Heteroarylalkyl und eine gegebenenfalls substituierte Aminogruppe steht,
R8 und R16
in den Resten (C-7) und (F-7) auch zusammen mit dem N-Atom, an das sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring bilden können, der ein oder mehrere weitere Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann,
R17
für einen Rest aus der Reihe jeweils gegebenenfalls substituiertes Alkyl, Alkoxy, Alkenyl und Alkinyl, jeweils gegebenenfalls substituiertes Cycloalkyl, Cycloalkylalkyl und Cycloalkenyl, in welchen die Ringe mindestens ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff enthalten können, jeweils gegebenenfalls substituiertes Aryl, Heteroaryl, Arylalkyl und Heteroarylalkyl und eine gegebenenfalls substituierte Aminogruppe steht,
R8 und R17
in den Resten (C-8) und (F-8) auch zusammen mit der N-C(X) Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring bilden können, der ein oder mehrere weitere Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann,
Y1 und Y2
unabhängig voneinander für C=O oder S(O)2 stehen,
R22
im Fall, dass R2 für g) steht, für einen Rest aus der Reihe Wasserstoff, Alkyl, Halogenalkyl, Cyanoalkyl, Alkenyl, Halogenalkenyl, Alkinyl, Halogenalkinyl, Alkoxy, Halogenalkoxy, gegebenenfalls durch Halogen substituiertes Alkoxyalkyl, gegebenenfalls durch Halogen substituiertes Bis(alkoxy)alkyl, gegebenenfalls durch Halogen substituiertes Alkylsulfanylalkyl, gegebenenfalls durch Halogen substituiertes Alkylcarbonylalkyl, gegebenenfalls durch Halogen substituiertes Alkylsulfinylalkyl, gegebenenfalls durch Halogen substituiertes Alkylsulfonylalkyl, Dialkylaminosulfanylalkyl, Dialkylaminosulfinylalkyl, Dialkylaminosulfonylalkyl, gegebenenfalls durch Halogen substituiertes Alkoxycarbonylalkyl, gegebenenfalls durch Halogen substituiertes Alkinyloxy, Dialkylaminocarbonylalkyl, N-Alkyl-N-Cycloalkylaminocarbonylalkyl, Heterocyclyl-carbonylalkyl, Alkylsulfanyl, Halogenalkylsulfanyl, Alkylsulfinyl, Halogenalkylsulfinyl, Alkylsulfonyl, Halogenalkylsulfonyl, gegebenenfalls durch Halogen, Cyano, Nitro, Alkyl, Cycloalkyl, Halogenalkyl, Alkoxy, Halogenalkoxy, Alkoxycarbonyl, Halogenalkoxycarbonyl oder Hetaryl (welches gegebenenfalls selbst durch Alkyl oder Halogen substituiert ist) substituiertes Cycloalkyl, gegebenenfalls durch Halogen, Cyano, Nitro, Alkyl, Halogenalkyl, Cycloalkyl, Alkoxy, Halogenalkoxy, Alkoxycarbonyl, Halogenalkoxycarbonyl oder Hetaryl (welches gegebenenfalls selbst durch Alkyl oder Halogen substituiert ist) substituiertes Cycloalkylalkyl, gegebenenfalls substituiertes Heterocyclyl, gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, Hydroxy, Alkyl, Halogenalkyl, Cycloalkyl (welches gegebenenfalls substituiert ist), Alkoxy, Halogenalkoxy, Alkylthio, Halogenalkylthio, Alkylsulfinyl, Alkylsulfonyl, Halogenalkylsulfinyl, Halogenalkylsulfonyl, Amino, Alkylamino, Dialkylamino, Alkylcarbonylamino, Alkoxycarbonylamino, Alkoxyalkyl, Halogenalkoxyalkyl, Alkenyl, Alkinyl, Cycloalkylalkyl, Alkylcarbonyl, Alkoxycarbonyl oder Aminocarbonyl substituiertes Heterocyclylalkyl, gegebenenfalls durch Halogen, Cyano, Nitro, Hydroxy, Amino, Alkyl, Halogenalkyl, Cycloalkyl (welches gegebenenfalls substituiert ist)Alkoxy oder Halogenalkoxy substituiertes Aryl, gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, Hydroxy, Amino, Alkyl, Cycloalkyl (welches gegebenenfalls substituiert ist), Halogenalkyl, Alkoxy oder Halogenalkoxy substituiertes Arylalkyl, gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, Hydroxy, Alkyl, Halogenalkyl, Cycloalkyl (welches gegebenenfalls substituiert ist), Alkoxy, Halogenalkoxy, Alkylthio, Halogenalkylthio, Alkylsulfinyl, Alkylsulfonyl, Halogenalkylsulfinyl, Halogenalkylsulfonyl, Amino, Alkylamino, Dialkylamino, Alkylcarbonylamino, Alkoxycarbonylamino, Alkoxyalkyl, Halogenalkoxyalkyl, Alkenyl, Alkinyl, Cycloalkylalkyl, Alkylcarbonyl, Alkoxycarbonyl oder Aminocarbonyl substituiertes Hetarylalkyl steht, oder, im Fall, dass R2 für c), d) oder g) steht,
R22
für einen D-Rest aus der Reihe (D-1) bis (D-3)
Figure imgb0059
 worin
X1
für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Nitro, Alkyl, Halogenalkyl, Cycloalkyl, Alkoxy und Halogenalkoxy steht,
R
für NR18R19 oder für einen jeweils gegebenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Alkoxyalkyl, Alkyl-S-alkyl, Alkyl-S(O)-alkyl, Alkyl-S(O)2-alkyl, R18-CO-alkyl, NR18R19-CO-alkyl, Cycloalkyl, Cycloalkenyl, Cycloalkylalkyl, Cycloalkenylalkyl, Heterocyclyl, Heterocyclylalkyl, Phenyl, Phenylalkyl, Hetaryl und Hetarylalkyl steht,
Y3
für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Alkyl, Cycloalkyl, Halogenalkyl, Alkoxy, Halogenalkoxy und NR20R21 steht,
W
für einen Rest aus der Reihe O, S, SO und SO2 steht,
R22
ferner für einen E-Rest aus der Reihe (E-1) bis (E-11)
Figure imgb0060
Figure imgb0061
Figure imgb0062
 der Reihe (E-18) bis (E-51)
Figure imgb0063
Figure imgb0064
Figure imgb0065
Figure imgb0066
Figure imgb0067
Figure imgb0068
Figure imgb0069
Figure imgb0070
Figure imgb0071
Figure imgb0072
 steht, oder, im Fall R2 = d),
R22
auch für einen E-Rest aus der Reihe E-12 bis E-17
Figure imgb0073
Figure imgb0074
 steht,
R18
für einen Rest aus der Reihe Wasserstoff, Hydroxy, jeweils gegebenenfalls substituiertes Alkyl, Alkoxy, Alkoxyalkyl, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl, Alkylcarbonyl, Alkoxycarbonyl, Alkenyl und Alkinyl, jeweils gegebenenfalls substituiertes Cycloalkyl, Cycloalkylalkyl, Cycloalkenyl und Cycloalkenylalkyl, in welchen die Ringe mindestens ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff enthalten können, jeweils gegebenenfalls substituiertes Aryl, Arylalkyl, Heteroaryl und Heteroarylalkyl und eine gegebenenfalls substituierte Aminogruppe steht,
R19
für einen Rest aus der Reihe Wasserstoff, für ein Alkali- oder Erdalkalimetallion oder für ein gegebenfalls einfach bis vierfach durch C1-C4-Alkyl substituiertes Ammoniumion oder für einen jeweils gegebenenfalls durch Halogen oder Cyano substituierten Rest aus der Reihe Alkyl, Alkoxy, Alkoxyalkyl, Alkylthioalkyl, Alkylsulfinylalkyl und Alkylsulfonylalkyl steht,
R20
für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Nitro, Amino, Hydroxy und jeweils gegebenenfalls substituiertes Alkyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkylalkyl, Alkoxy, Alkenyloxy, Alkinyloxy, Cycloalkyloxy, Alkylcarbonyloxy, Alkenylcarbonyloxy, Alkinylcarbonyloxy, Cycloalkylcarbonyloxy, Alkoxycarbonyloxy, Alkylsulfonyloxy, Alkylamino, Alkenylamino, Alkinylamino, Cycloalkylamino, Alkylthio, Halogenalkylthio, Alkenylthio, Alkinylthio, Cycloalkylthio, Alkylsulfinyl, Alkylsulfonyl, Alkylcarbonyl, Alkoxyiminoalkyl, Alkoxycarbonyl, Aminocarbonyl, Alkylaminocarbonyl, Dialkylaminocarbonyl, Aminothiocarbonyl, Alkylaminosulfonyl, Alkylsulfonylamino, Alkylcarbonylamino, Alkenylcarbonylamino, Alkinylcarbonylamino, Cycloalkylcarbonylamino, Alkoxycarbonylamino, Alkylthiocarbonylamino, Bicycloalkyl, Aryl, Aryloxy, Heteroaryl und Heteroaryloxy steht, wobei die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Cyano, Nitro, Hydroxy, Amino, Alkyl und Halogenalkyl,
R21
für einen Rest aus der Reihe Wasserstoff, Alkyl, Cycloalkyl, Halogenalkyl, Alkenyl, Alkinyl, Cycloalkylalkyl, Cyanoalkyl, Alkylcarbonyl, Alkenylcarbonyl, Halogenalkylcarbonyl, Halogenalkenylcarbonyl, Alkoxyalkyl, Alkoxycarbonyl, Alkylsulfonyl und Halogenalkylsulfonyl steht,
R23
für einen Rest aus der Reihe Wasserstoff, Alkyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkenyl, Alkoxy, Alkenyloxy, Alkinyloxy, Cycloalkyloxy, Alkylthioalkyl, Alkenylthioalkyl, Cyanoalkyl, Alkoxyalkyl steht
oder, für R2 = g),
R22 und R23
gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen Ring bilden, der ein oder mehrere weitere Heteroatome aus der Reihe Stickstoff, Sauerstoff und Schwefel enthalten kann, und
R24
für Wasserstoff oder einen jeweils gegebenenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Phenyl und Phenylalkyl steht und
R25
für Wasserstoff oder einen jeweils gegebenenfalls substituierten Rest aus der Reihe Alkyl, Alkenyl, Alkinyl, Phenyl und Phenylalkyl steht,
R26
für einen Rest aus der Reihe Wasserstoff, Alkyl, Halogenalkyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkylalkyl, Alkoxy-alkyl, Alkylsulfanyl, Halogenalkylsulfanyl, Alkylsulfinyl, Halogenalkylsulfinyl, Alkylsulfonyl, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl und Cyanoalkyl steht.
R27
für Wasserstoff, Alkyl, Halogenalkyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkylalkyl, Alkoxyalkyl, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl oder Cyanoalkyl steht.
The problem is solved, as well as other tasks not explicitly mentioned, which can be deduced or deduced from the relationships discussed herein, by novel compounds of the formula (I)
Figure imgb0001
 in which
A
for an A-residue from the series (Ab) to (Af)
Figure imgb0002
 wherein the dashed line represents the bond to the carbon atom of the bicyclic of formula (I) and
B 2
a radical selected from the group consisting of hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy and in each case optionally substituted cycloalkyl and cycloalkenyl,
Q
stands for oxygen or sulfur,
R 1
is a radical from the series hydrogen, alkyl, alkoxy and cyano,
R 2
a) for a B residue from the series
Figure imgb0003
Figure imgb0004
Figure imgb0005
Figure imgb0006
Figure imgb0007
Figure imgb0008
Figure imgb0009
Figure imgb0010
Figure imgb0011
 wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R 2
b) for a D radical from the series (D-1) to (D-3)
Figure imgb0012
 wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R 2
c) a radical of the formula
Figure imgb0013
 wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R 2
d) for a radical of the formula
Figure imgb0014
 wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R 2
e) for an F radical from the series (F-1) to (F-11)
Figure imgb0015
Figure imgb0016
Figure imgb0017
Figure imgb0018
 stands,
wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R 2
f) is a radical from the group consisting of haloalkyl and carboxyl,
R 2
g) for a radical of the formula
Figure imgb0019
 in which the dashed line denotes the bond to the carbon atom of the bicyclic compound of the formula (I),
wherein
G 2
is hydrogen or a radical from the series halogen, nitro, amino, cyano, alkylamino, haloalkylamino, dialkylamino, alkyl, haloalkyl, optionally substituted and optionally interrupted by one or more heteroatoms saturated or unsaturated cycloalkyl, cycloalkylalkyl, alkoxy, haloalkoxy, alkoxyalkyl, halogenated Alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, bis (alkoxy) alkyl, bis (haloalkoxy) alkyl, alkoxy (alkylsulfanyl) alkyl, alkoxy (alkylsulfinyl) alkyl, alkoxy (alkylsulfonyl) alkyl, bis (alkylsulfanyl) alkyl, bis (haloalkylsulfanyl) alkyl, Bis (hydroxyalkylsulfanyl) alkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alpha-hydroxyiminoalkoxycarbonylalkyl, alpha-alkoxyiminoalkoxycarbonylalkyl, C (X 2 ) NR 3 R 4 , NR 6 R 7 , alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, the heterocyclyl radicals dioxanyl , Dioxolanyl, dioxepanyl, dioxocanyl, oxathianyl, oxathiolanyl, oxathiepanyl, oxathi ocanyl, dithianyl, dithiolanyl, dithiepanyl, dithiocanyl, oxathianyloxide, oxathiolanyloxide, oxathialpanyloxide, oxathiocanyloxide, oxathianyl dioxide, oxathiolanyl dioxide, oxathiepanyl dioxide, oxathiocanyl dioxide, morpholinyl, triazolinonyl, oxazolinyl, dihydrooxadiazinyl, dihydrodioxazinyl, dihydrooxazolyl, dihydrooxazinyl and pyrazolinonyl (which in turn may be substituted by alkyl , Haloalkyl, alkoxy and alkoxyalkyl), phenyl (which in turn may itself be substituted by halogen, cyano, nitro, alkyl and haloalkyl), the heteroaryl radicals pyridyl, pyridyl-N-oxide, pyrimidyl, imidazolyl, pyrazolyl, oxazolyl, thiazolyl, furanyl, Thienyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyrazinyl, triazinyl, tetrazinyl and isoquinolinyl (which in turn may themselves be substituted by halogen, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxyalkyl, alkylthio, alkylthioalkyl and cycloalkyl) and the heteroarylalkyl radicals triazolylalkyl, Pyridylalkyl, Pyri midylalkyl and oxadiazolylalkyl (which in turn may themselves be substituted by halogen and alkyl),
or
G 2
for a C-radical from the series (C-1) to (C-9)
Figure imgb0020
Figure imgb0021
Figure imgb0022
 wherein the dashed line indicates the bond to the B radicals,
X
stands for oxygen or sulfur,
X
stands for oxygen or sulfur,
X 1
a radical selected from the group consisting of hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, cycloalkyl, alkoxy and haloalkoxy,
X 2
is oxygen, sulfur, NR 5 or NOH,
L
stands for oxygen or sulfur,
VZ
R 24 is CH-CHR 25 or R 24 is C = CR 25 ,
n
stands for 1 or 2,
m
is 1, 2, 3 or 4,
R
for NR 18 R 19 or for an optionally substituted radical from the series alkyl, alkenyl, alkynyl, alkoxyalkyl, alkyl-S-alkyl, alkyl-S (O) -alkyl, alkyl-S (O) 2 -alkyl, R 18 -CO-alkyl, NR 18 R 19 is -CO-alkyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, phenyl, phenylalkyl, hetaryl and hetarylalkyl,
R 3
is hydrogen or alkyl,
R 4
a radical selected from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, aryl, arylalkyl and hetarylalkyl,
R 5
a radical selected from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, aryl, arylalkyl and hetarylalkyl, or
R 3 and R 4
together with the nitrogen atom to which they are attached form a ring which may contain one or more further nitrogen, oxygen and sulfur heteroatoms, or
R 3 and R 5
together with the nitrogen atoms to which they are attached form a ring,
R 6
is hydrogen or alkyl,
R 7
a radical selected from hydrogen, alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy, haloalkoxy, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, aryl, arylalkyl or hetarylalkyl, or
R 6 and R 7
together with the nitrogen atom to which they are attached form a ring which may contain one or more further nitrogen, oxygen and sulfur heteroatoms,
R 8
a radical from the series consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkoxy, haloalkoxy, alkenyl, alkoxyalkyl, in each case optionally halogen-substituted alkylcarbonyl and alkylsulfonyl, optionally halogen-substituted alkoxycarbonyl, optionally halogen, alkyl, alkoxy, haloalkyl and cyano-substituted cycloalkylcarbonyl is, or represents a cation or an optionally substituted by alkyl or arylalkyl ammonium ion,
R 9
a radical from the series in each case optionally substituted alkyl, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings may contain at least one heteroatom from the series sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen each optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group,
R 8 and R 9
in the radicals (C-1) and (F-1), together with the NS (O) n group to which they are attached, can form a saturated or unsaturated and optionally substituted 4- to 8-membered ring, the one or more further heteroatoms from the series sulfur, Oxygen (where oxygen atoms are not allowed to be immediately adjacent) and nitrogen and / or at least one carbonyl group,
R 10
is hydrogen or alkyl,
R 8 and R 10
in the radicals (C-2) and (F-2) also together with the N atoms to which they are attached, may represent a saturated or unsaturated and optionally substituted 4- to 8-membered ring containing at least one further heteroatom from the series sulfur, oxygen (oxygen atoms may not be immediately adjacent) and contain nitrogen and / or at least one carbonyl group,
R 9 and R 10
in the radicals (C-2) and (F-2) also together with the NS (O) n group to which they are attached, can form a saturated or unsaturated and optionally substituted 4- to 8-membered ring, the or a plurality of further heteroatoms from the group consisting of sulfur, oxygen (where oxygen atoms are not allowed to be immediately adjacent) and nitrogen and / or at least one carbonyl group,
R 11
represents an optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyl, cycloalkyloxy, cycloalkenyloxy, cycloalkylalkoxy, alkylthio, alkenylthio, phenoxy, phenylthio, benzyloxy, benzylthio, heteroaryloxy, heteroarylthio, heteroarylalkoxy and heteroarylalkylthio,
R 12
represents an optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyl, cycloalkyloxy, cycloalkenyloxy, cycloalkylalkoxy, alkylthio, alkenylthio, phenoxy, phenylthio, benzyloxy, benzylthio, heteroaryloxy, heteroarylthio, heteroarylalkoxy and heteroarylalkylthio,
R 11 and R 12
in the radicals (C-3) and (F-3) may also together with the phosphorus atom to which they are attached form a saturated or unsaturated and optionally substituted 5- to 7-membered ring containing one or two heteroatoms from the Oxygen (where oxygen atoms are not allowed to be immediately adjacent) and sulfur,
R 13
represents an optionally substituted radical from the series alkyl, alkenyl, alkynyl, phenyl and phenylalkyl,
R 14
represents an optionally substituted radical from the series alkyl, alkenyl, alkynyl, phenyl and phenylalkyl,
R 15
each of a residue from the series optionally substituted alkyl, alkenyl and alkynyl, each optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings may contain at least one heteroatom selected from the group consisting of sulfur, oxygen (where oxygen atoms may not be immediately adjacent) and nitrogen, in each case optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group,
R 8 and R 15
in the radicals (C-6) and (F-6) together with the NS (O) n group to which they are attached, it is also possible to form a saturated or unsaturated and optionally substituted 4- to 8-membered ring or a plurality of further heteroatoms from the group consisting of sulfur, oxygen (where oxygen atoms are not allowed to be immediately adjacent) and nitrogen and / or at least one carbonyl group,
R 16
a radical selected from the group consisting of hydrogen, in each case optionally substituted alkyl, alkoxy, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings are at least one heteroatom selected from the group consisting of sulfur, oxygen (oxygen atoms may not be immediately adjacent) and each may contain nitrogen, each optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group,
R 8 and R 16
in the radicals (C-7) and (F-7) together with the N-atom to which they are attached, it is also possible to form a saturated or unsaturated and optionally substituted 4- to 8-membered ring which contains one or more further radicals Heteroatoms from the series sulfur, oxygen (oxygen atoms may not be immediately adjacent) and contain nitrogen and / or at least one carbonyl group,
R 17
in each case a radical from the series optionally substituted alkyl, alkoxy, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings at least one heteroatom selected from sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen each optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group,
R 8 and R 17
in the radicals (C-8) and (F-8), together with the NC (X) group to which they are attached, can form a saturated or unsaturated and optionally substituted 4- to 8-membered ring, the one or several further heteroatoms from the series sulfur, oxygen (oxygen atoms may not be immediately adjacent) and contain nitrogen and / or at least one carbonyl group,
R 18
a radical selected from the group consisting of hydrogen, hydroxyl, in each case optionally substituted alkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkylcarbonyl, alkoxycarbonyl, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, Cycloalkylalkyl, cycloalkenyl and cycloalkenylalkyl in which the rings may contain at least one heteroatom selected from the group consisting of sulfur, oxygen (where oxygen atoms are not immediately adjacent) and nitrogen, each optionally substituted aryl, arylalkyl, heteroaryl and heteroarylalkyl and an optionally substituted amino group,
R 19
a radical selected from the group consisting of hydrogen, an alkali or alkaline earth metal ion or an optionally monosubstituted to monosubstituted by C 1 -C 4 -alkyl-substituted ammonium ion or an optionally halogen or cyano-substituted radical from the series alkyl, alkoxy, alkoxyalkyl , Alkylthioalkyl, alkylsulfinylalkyl and alkylsulfonylalkyl,
Y 1 and Y 2
independently represent C = O or S (O) 2 ,
Y 3
a radical selected from among hydrogen, halogen, cyano, alkyl, cycloalkyl, haloalkyl, alkoxy, haloalkoxy and NR 20 R 21 ,
W
is a radical from the series O, S, SO and SO 2 ,
R 22
a radical from the series consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, optionally halogen-substituted alkoxyalkyl, optionally halogen-substituted bis (alkoxy) alkyl, optionally halogen-substituted alkylsulfanylalkyl, optionally Halogen-substituted alkylcarbonylalkyl, alkylsulphinylalkyl optionally substituted by halogen, alkylsulphonylalkyl optionally substituted by halogen, dialkylaminosulphanylalkyl, dialkylaminosulphinylalkyl, dialkylaminosulphonylalkyl, alkoxycarbonyl optionally substituted by halogen, optionally alkoxycarbonylalkyl substituted by halogen, optionally halogen-substituted alkynyloxy, optionally halogen-substituted alkynyloxycarbonyl, dialkylaminocarbonyl, N- Alkyl-N-cycloalkylaminocarbonyl, dialkylaminocarbonylalkyl, N-alkyl-N-cycloalkylaminocarbonylalkyl, heterocyclylcarbonylalkyl , Alkylsulfanyl, haloalkylsulfanyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, optionally substituted by halogen, cyano, nitro, alkyl, cycloalkyl, haloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, haloalkoxycarbonyl or hetaryl (which is optionally itself substituted by alkyl or halogen) substituted cycloalkyl, optionally substituted by halogen, cyano, nitro, alkyl, haloalkyl, cycloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, haloalkoxycarbonyl or hetaryl (which is optionally itself substituted by alkyl or halogen) substituted cycloalkylcarbonyl, optionally substituted by halogen, cyano, nitro, alkyl, haloalkyl, cycloalkyl , Alkoxy, haloalkoxy, alkoxycarbonyl, haloalkoxycarbonyl or hetaryl (which is optionally itself substituted by alkyl or halogen) substituted cycloalkylalkyl, optionally substituted heterocyclyl, optionally substituted by halogen, Cyano (also in the alkyl portion), nitro, hydroxy, alkyl, haloalkyl, cycloalkyl (which is optionally substituted), alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, amino, alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonylamino, alkoxyalkyl , Haloalkoxyalkyl, alkenyl, alkynyl, cycloalkylalkyl, alkylcarbonyl, alkoxycarbonyl or aminocarbonyl-substituted heterocyclylalkyl, optionally substituted by halogen, cyano, nitro, hydroxy, amino, alkyl, haloalkyl, cycloalkyl (which is optionally substituted) alkoxy or haloalkoxy-substituted aryl, optionally halogen, Cyano (also in the alkyl portion), nitro, hydroxy, amino, alkyl, cycloalkyl (which is optionally substituted), haloalkyl, alkoxy or haloalkoxy-substituted arylalkyl, optionally substituted by halogen, cyano (also in the alkyl portion), nitro, hydroxy, alkyl, haloalkyl, Cycloalkyl (which is optionally substituted t), alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, amino, alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonylamino, alkoxyalkyl, haloalkoxyalkyl, alkenyl, alkynyl, cycloalkylalkyl, alkylcarbonyl, alkoxycarbonyl or aminocarbonyl substituted hetarylalkyl, or
R 22
for a D radical from the series (D-1) to (D-3)
Figure imgb0023
 an E-residue from the series (E-1) to (E-11)
Figure imgb0024
Figure imgb0025
Figure imgb0026
 row (E-18) to (E-51)
Figure imgb0027
Figure imgb0028
Figure imgb0029
Figure imgb0030
Figure imgb0031
Figure imgb0032
Figure imgb0033
Figure imgb0034
Figure imgb0035
Figure imgb0036
 stands, or
in case R 2 = d),
R 22
also for an E-rest from the series E-12 to E-17
Figure imgb0037
Figure imgb0038
 wherein here and later the dashed line denotes the bond to the corresponding atom in the radicals c), d) and g),
R 20
a radical from the group consisting of hydrogen, halogen, cyano, nitro, amino, hydroxy and in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, alkylcarbonyloxy, alkenylcarbonyloxy, alkynylcarbonyloxy, cycloalkylcarbonyloxy, alkoxycarbonyloxy, alkylsulfonyloxy , Alkylamino, alkenylamino, alkynylamino, cycloalkylamino, alkylthio, haloalkylthio, alkenylthio, alkynylthio, cycloalkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxyiminoalkyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminosulfonyl, alkylsulfonylamino, alkylcarbonylamino, alkenylcarbonylamino, alkynylcarbonylamino, cycloalkylcarbonylamino, alkoxycarbonylamino , Alkylthiocarbonylamino, bicycloalkyl, aryl, aryloxy, heteroaryl and heteroaryloxy, where the substituents are independently selected from halogen, cyano, nitro, hydroxy, amino, alkyl and haloalkyl,
R 21
a radical selected from the group consisting of hydrogen, alkyl, cycloalkyl, haloalkyl, alkenyl, alkynyl, cycloalkylalkyl, cyanoalkyl, alkylcarbonyl, alkenylcarbonyl, haloalkylcarbonyl, haloalkenylcarbonyl, alkoxyalkyl, alkoxycarbonyl, alkylsulfonyl and haloalkylsulfonyl,
R 23
a radical selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, alkylthioalkyl, alkenylthioalkyl, cyanoalkyl, alkoxyalkyl,
or, for R 2 = c) or g),
R 22 and R 23
together with the nitrogen atom to which they are attached form a ring which may contain one or more further nitrogen, oxygen and sulfur heteroatoms, and
R 24
represents hydrogen or a respectively optionally substituted radical from the series alkyl, alkenyl, alkynyl, phenyl and phenylalkyl and
R 25
represents hydrogen or a respectively optionally substituted radical from the series alkyl, alkenyl, alkynyl, phenyl and phenylalkyl,
R 26
a radical selected from the group consisting of hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkylsulfanyl, haloalkylsulfanyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl and cyanoalkyl.
R 27
is hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl or cyanoalkyl, and
Compounds of the formula (I) in which
A
for the A-rest
Figure imgb0039
 in which the dashed line denotes the bond to the carbon atom of the bicyclic compound of the formula (I), and
G 1
stands for N or CB 1 ,
B 1
a radical selected from the group consisting of hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy and in each case optionally substituted cycloalkyl and cycloalkenyl,
B 2
a radical selected from the group consisting of hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy and in each case optionally substituted cycloalkyl and cycloalkenyl,
T
stands for oxygen or a pair of electrons,
Q
stands for oxygen or sulfur,
R 1
is a radical from the series hydrogen, alkyl, alkoxy and cyano,
R 2
a) for a B residue from the series
Figure imgb0040
Figure imgb0041
Figure imgb0042
Figure imgb0043
Figure imgb0044
Figure imgb0045
Figure imgb0046
Figure imgb0047
Figure imgb0048
 wherein the dashed line marks the bond to the carbon atom of the bicycle of formula (I), or
R 2
c) a radical of the formula
Figure imgb0049
 wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R 2
d) for a radical of the formula
Figure imgb0050
 wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R 2
e) for an F residue from the series
Figure imgb0051
Figure imgb0052
Figure imgb0053
Figure imgb0054
 wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R 2
f) is a radical from the group consisting of haloalkyl and carboxyl,
R 2
g) for a radical of the formula
Figure imgb0055
 wherein the dotted line represents the bond to the carbon atom of the bicyclic moiety of formula (I) wherein
G 2
is hydrogen or a radical from the series halogen, nitro, amino, cyano, alkylamino, haloalkylamino, dialkylamino, alkyl, haloalkyl, optionally substituted and optionally interrupted by one or more heteroatoms saturated or unsaturated cycloalkyl, cycloalkylalkyl, alkoxy, haloalkoxy, alkoxyalkyl, halogenated Alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, bis (alkoxy) alkyl, bis (haloalkoxy) alkyl, alkoxy (alkylsulfanyl) alkyl, alkoxy (alkylsulfinyl) alkyl, alkoxy (alkylsulfonyl) alkyl, bis (alkylsulfanyl) alkyl, bis (haloalkylsulfanyl) alkyl, Bis (hydroxyalkylsulfanyl) alkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alpha-hydroxyiminoalkoxycarbonylalkyl, alpha-alkoxyiminoalkoxycarbonylalkyl, C (X 2 ) NR 3 R 4 , NR 6 R 7 , alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, the heterocyclyl radicals dioxanyl , Dioxolanyl, dioxepanyl, dioxocanyl, oxathianyl, oxathiolanyl, oxathiepanyl, oxathi ocanyl, dithianyl, dithiolanyl, dithiepanyl, dithiocanyl, oxathianyloxide, oxathiolanyloxide, oxathialpanyloxide, oxathiocanyloxide, oxathianyl dioxide, oxathiolanyl dioxide, oxathiepanyl dioxide, oxathiocanyl dioxide, morpholinyl, triazolinonyl, oxazolinyl, dihydrooxadiazinyl, dihydrodioxazinyl, dihydrooxazolyl, dihydrooxazinyl and pyrazolinonyl (which in turn may be substituted by alkyl , Haloalkyl, alkoxy and alkoxyalkyl), phenyl (which in turn may itself be substituted by halogen, cyano, nitro, alkyl and haloalkyl), the heteroaryl radicals pyridyl, pyridyl-N-oxide, pyrimidyl, imidazolyl, pyrazolyl, oxazolyl, thiazolyl, furanyl, Thienyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyrazinyl, triazinyl, tetrazinyl and isoquinolinyl (which in turn may themselves be substituted by halogen, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxyalkyl, alkylthio, alkylthioalkyl and cycloalkyl) and the heteroarylalkyl radicals triazolylalkyl, Pyridylalkyl, Pyri haloalkyl and oxadiazolylalkyl (which in turn may themselves be substituted by halogen and alkyl), or
G 2
for a C-radical from the series (C-1) to (C-9)
Figure imgb0056
Figure imgb0057
Figure imgb0058
 wherein the dashed line indicates the bond to the B radicals,
X
stands for oxygen or sulfur,
X 2
is oxygen, sulfur, NR 5 or NOH,
L
stands for oxygen or sulfur,
VZ
R 24 is CH-CHR 25 or R 24 is C = CR 25 ,
n
stands for 1 or 2,
m
is 1, 2, 3 or 4,
R 3
is hydrogen or alkyl,
R 4
a radical selected from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, aryl, arylalkyl and hetarylalkyl,
R 5
a radical selected from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, aryl, arylalkyl and hetarylalkyl, or
R 3 and R 4
together with the nitrogen atom to which they are attached form a ring which may contain one or more further nitrogen, oxygen and sulfur heteroatoms, or
R 3 and R 5
together with the nitrogen atoms to which they are attached form a ring,
R 6
is hydrogen or alkyl,
R 7
a radical selected from hydrogen, alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy, haloalkoxy, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, aryl, arylalkyl or hetarylalkyl, or
R 6 and R 7
together with the nitrogen atom to which they are attached form a ring which may contain one or more further nitrogen, oxygen and sulfur heteroatoms,
R 8
a radical from the series consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkoxy, haloalkoxy, alkenyl, alkoxyalkyl, in each case optionally halogen-substituted alkylcarbonyl and alkylsulfonyl, optionally halogen-substituted alkoxycarbonyl, optionally halogen, alkyl, alkoxy, haloalkyl and cyano-substituted cycloalkylcarbonyl is, or represents a cation or an optionally substituted by alkyl or arylalkyl ammonium ion,
R 9
a radical from the series in each case optionally substituted alkyl, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings may contain at least one heteroatom from the series sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen each optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group,
R 8 and R 9
in the radical (C-1) together with the NS (O) n group to which they are attached, can form a saturated or unsaturated and optionally substituted 4- to 8-membered ring which contains one or more further heteroatoms from the Sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen and / or at least one carbonyl group,
R 10
is hydrogen or alkyl,
R 8 and R 10
in the radicals (C-2) and (F-2) also together with the N atoms to which they are attached, may represent a saturated or unsaturated and optionally substituted 4- to 8-membered ring containing at least one further heteroatom from the series sulfur, oxygen (oxygen atoms may not be immediately adjacent) and contain nitrogen and / or at least one carbonyl group,
R 9 and R 10
in the radicals (C-2) and (F-2) also together with the NS (O) n group to which they are attached, can form a saturated or unsaturated and optionally substituted 4- to 8-membered ring, the or a plurality of further heteroatoms from the group consisting of sulfur, oxygen (where oxygen atoms are not allowed to be immediately adjacent) and nitrogen and / or at least one carbonyl group,
R 11
represents an optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyl, cycloalkyloxy, cycloalkenyloxy, cycloalkylalkoxy, alkylthio, alkenylthio, phenoxy, phenylthio, benzyloxy, benzylthio, heteroaryloxy, heteroarylthio, heteroarylalkoxy and heteroarylalkylthio,
R 12
represents an optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyl, cycloalkyloxy, cycloalkenyloxy, cycloalkylalkoxy, alkylthio, alkenylthio, phenoxy, phenylthio, benzyloxy, benzylthio, heteroaryloxy, heteroarylthio, heteroarylalkoxy and heteroarylalkylthio,
R 11 and R 12
in the radicals (C-3) and (F-3) may also together with the phosphorus atom to which they are attached form a saturated or unsaturated and optionally substituted 5- to 7-membered ring containing one or two heteroatoms from the Oxygen (where oxygen atoms are not allowed to be immediately adjacent) and sulfur,
R 13
represents an optionally substituted radical from the series alkyl, alkenyl, alkynyl, phenyl and phenylalkyl,
R 14
represents an optionally substituted radical from the series alkyl, alkenyl, alkynyl, phenyl and phenylalkyl,
R 15
a radical from the series in each case optionally substituted alkyl, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings may contain at least one heteroatom from the series sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen each optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group,
R 8 and R 15
in the radicals (C-6) and (F-6) together with the NS (O) n group to which they are attached, it is also possible to form a saturated or unsaturated and optionally substituted 4- to 8-membered ring or a plurality of further heteroatoms from the group consisting of sulfur, oxygen (where oxygen atoms are not allowed to be immediately adjacent) and nitrogen and / or at least one carbonyl group,
R 16
a radical selected from the group consisting of hydrogen, in each case optionally substituted alkyl, alkoxy, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings are at least one heteroatom selected from the group consisting of sulfur, oxygen (oxygen atoms may not be immediately adjacent) and each may contain nitrogen, each optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group,
R 8 and R 16
in the radicals (C-7) and (F-7) together with the N-atom to which they are attached, it is also possible to form a saturated or unsaturated and optionally substituted 4- to 8-membered ring which contains one or more further radicals Heteroatoms from the series sulfur, oxygen (oxygen atoms may not be immediately adjacent) and contain nitrogen and / or at least one carbonyl group,
R 17
in each case a radical from the series optionally substituted alkyl, alkoxy, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings at least one heteroatom selected from sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen each optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group,
R 8 and R 17
in the radicals (C-8) and (F-8), together with the NC (X) group to which they are attached, can form a saturated or unsaturated and optionally substituted 4- to 8-membered ring, the one or several further heteroatoms from the series sulfur, oxygen (oxygen atoms may not be immediately adjacent) and contain nitrogen and / or at least one carbonyl group,
Y 1 and Y 2
independently represent C = O or S (O) 2 ,
R 22
in the case where R 2 is g), a radical selected from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, optionally halogen-substituted alkoxyalkyl, optionally halogen-substituted bis (alkoxy alkyl, optionally halogen-substituted alkylcarbonylalkyl, optionally alkyl-substituted haloalkylsulfinylalkyl, optionally halogen-substituted alkylsulfonylalkyl, dialkylaminosulfanylalkyl, dialkylaminosulfinylalkyl, dialkylaminosulfonylalkyl, optionally halogen-substituted alkoxycarbonylalkyl, optionally halogen-substituted alkynyloxy, dialkylaminocarbonylalkyl, N-alkyl -N-cycloalkylaminocarbonylalkyl, heterocyclylcarbonylalkyl, alkylsulfanyl, haloalkylsulfanyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, optionally by halogen, cyano , Nitro, alkyl, cycloalkyl, haloalkyl, alkoxy, haloalkoxy, Alkoxycarbonyl, haloalkoxycarbonyl or hetaryl (which is optionally itself substituted by alkyl or halogen) substituted cycloalkyl, optionally substituted by halogen, cyano, nitro, alkyl, haloalkyl, cycloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, haloalkoxycarbonyl or hetaryl (which may itself be alkyl or halogen substituted cycloalkylalkyl, optionally substituted heterocyclyl, optionally substituted by halogen, cyano (also in the alkyl portion), nitro, hydroxy, alkyl, haloalkyl, cycloalkyl (which is optionally substituted), alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylsulfinyl , Haloalkylsulfonyl, amino, alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonylamino, alkoxyalkyl, haloalkoxyalkyl, alkenyl, alkynyl, cycloalkylalkyl, alkylcarbonyl, alkoxycarbonyl or aminocarbonyl-substituted heterocyclylalkyl, optionally substituted by halogen, cyano, nitro, hydr oxy, amino, alkyl, haloalkyl, cycloalkyl (which is optionally substituted) alkoxy or haloalkoxy-substituted aryl, optionally substituted by halogen, cyano (also in the alkyl portion), nitro, hydroxy, amino, alkyl, cycloalkyl (which is optionally substituted), haloalkyl, Alkoxy or haloalkoxy-substituted arylalkyl, optionally substituted by halogen, cyano (also in the alkyl portion), nitro, hydroxy, alkyl, haloalkyl, cycloalkyl (which is optionally substituted), alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, amino , Alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonylamino, alkoxyalkyl, haloalkoxyalkyl, alkenyl, alkynyl, cycloalkylalkyl, alkylcarbonyl, alkoxycarbonyl or aminocarbonyl-substituted hetarylalkyl, or, in the case where R 2 is c), d) or g),
R 22
for a D radical from the series (D-1) to (D-3)
Figure imgb0059
 wherein
X 1
a radical selected from the group consisting of hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, cycloalkyl, alkoxy and haloalkoxy,
R
for NR 18 R 19 or for an optionally substituted radical from the series alkyl, alkenyl, alkynyl, alkoxyalkyl, alkyl-S-alkyl, alkyl-S (O) -alkyl, alkyl-S (O) 2 -alkyl, R 18 -CO-alkyl, NR 18 R 19 is -CO-alkyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, phenyl, phenylalkyl, hetaryl and hetarylalkyl,
Y 3
a radical selected from among hydrogen, halogen, cyano, alkyl, cycloalkyl, haloalkyl, alkoxy, haloalkoxy and NR 20 R 21 ,
W
is a radical from the series O, S, SO and SO 2 ,
R 22
furthermore for an E radical from the series (E-1) to (E-11)
Figure imgb0060
Figure imgb0061
Figure imgb0062
 row (E-18) to (E-51)
Figure imgb0063
Figure imgb0064
Figure imgb0065
Figure imgb0066
Figure imgb0067
Figure imgb0068
Figure imgb0069
Figure imgb0070
Figure imgb0071
Figure imgb0072
 stands, or, in the case R 2 = d),
R 22
also for an E-rest from the series E-12 to E-17
Figure imgb0073
Figure imgb0074
 stands,
R 18
a radical from the series hydrogen, hydroxy, in each case optionally substituted alkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkylcarbonyl, Alkoxycarbonyl, alkenyl and alkynyl, each optionally substituted cycloalkyl, cycloalkylalkyl, cycloalkenyl and cycloalkenylalkyl in which the rings may contain at least one heteroatom selected from sulfur, oxygen (where oxygen atoms are not immediately adjacent) and nitrogen, each optionally substituted aryl, arylalkyl , Heteroaryl and heteroarylalkyl and an optionally substituted amino group,
R 19
a radical selected from the group consisting of hydrogen, an alkali or alkaline earth metal ion or an optionally monosubstituted to monosubstituted by C 1 -C 4 -alkyl-substituted ammonium ion or an optionally halogen or cyano-substituted radical from the series alkyl, alkoxy, alkoxyalkyl , Alkylthioalkyl, alkylsulfinylalkyl and alkylsulfonylalkyl,
R 20
a radical from the group consisting of hydrogen, halogen, cyano, nitro, amino, hydroxy and in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, alkylcarbonyloxy, alkenylcarbonyloxy, alkynylcarbonyloxy, cycloalkylcarbonyloxy, alkoxycarbonyloxy, alkylsulfonyloxy , Alkylamino, alkenylamino, alkynylamino, cycloalkylamino, alkylthio, haloalkylthio, alkenylthio, alkynylthio, cycloalkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxyiminoalkyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminosulfonyl, alkylsulfonylamino, alkylcarbonylamino, alkenylcarbonylamino, alkynylcarbonylamino, cycloalkylcarbonylamino, alkoxycarbonylamino , Alkylthiocarbonylamino, bicycloalkyl, aryl, aryloxy, heteroaryl and heteroaryloxy, where the substituents are independently selected from halogen, cyano, nitro, hydroxy, amino, alkyl and haloalkyl,
R 21
a radical selected from the group consisting of hydrogen, alkyl, cycloalkyl, haloalkyl, alkenyl, alkynyl, cycloalkylalkyl, cyanoalkyl, alkylcarbonyl, alkenylcarbonyl, haloalkylcarbonyl, haloalkenylcarbonyl, alkoxyalkyl, alkoxycarbonyl, alkylsulfonyl and haloalkylsulfonyl,
R 23
a radical selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, alkylthioalkyl, alkenylthioalkyl, cyanoalkyl, alkoxyalkyl
or, for R 2 = g),
R 22 and R 23
together with the nitrogen atom to which they are attached form a ring which may contain one or more further nitrogen, oxygen and sulfur heteroatoms, and
R 24
represents hydrogen or a respectively optionally substituted radical from the series alkyl, alkenyl, alkynyl, phenyl and phenylalkyl and
R 25
represents hydrogen or a respectively optionally substituted radical from the series alkyl, alkenyl, alkynyl, phenyl and phenylalkyl,
R 26
a radical selected from the group consisting of hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkylsulfanyl, haloalkylsulfanyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl and cyanoalkyl.
R 27
is hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl or cyanoalkyl.

Weiterhin wurde gefunden, dass die Verbindungen der Formel (I) und auch diejenigen in der Tabelle 1 aufgeführten Verbindungen, die nicht unter die Formel (I) fallen, eine gute Wirksamkeit als Schädlingsbekämpfungsmittel, beispielsweise gegen Arthropoden und insbesondere Insekten, besitzen und darüber hinaus in der Regel insbesondere gegenüber Kulturpflanzen sehr gut pflanzenverträglich sind und/oder über günstige toxikologische und/oder günstige umweltrelevante Eigenschaften verfügen.Furthermore, it has been found that the compounds of the formula (I) and also those compounds listed in Table 1 which do not fall under the formula (I) have a good activity as pesticides, for example against arthropods and in particular insects, and in addition the rule especially against crop plants are very good plant compatibility and / or have favorable toxicological and / or favorable environmental properties.

Vorzugsbereich (1): Bevorzugt sind Verbindungen der Formel (I), in welchen

A
für einen A-Rest aus der Reihe (A-b) und (A-f)
Figure imgb0075
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, und
B2
für einen Rest aus der Reihe Wasserstoff, Halogen, C1-C6-Alkyl und C1-C4-Halogenalkyl steht,
Q
für Schwefel steht,
R1
für einen Rest aus der Reihe Wasserstoff, C1-C6-Alkyl und C1-C6-Alkoxy steht,
R2
a) für einen B-Rest aus der Reihe
Figure imgb0076
Figure imgb0077
Figure imgb0078
Figure imgb0079
Figure imgb0080
Figure imgb0081
Figure imgb0082
Figure imgb0083
Figure imgb0084
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder
R2
b) für einen D-Rest aus der Reihe (D-1) bis (D-3)
Figure imgb0085
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder
R2
c) für einen Rest der Formel
Figure imgb0086
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder
R2
d) für einen Rest der Formel
Figure imgb0087
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder
R2
e) für einen F-Rest aus der Reihe (F-1), (F-8), (F-10) und (F-11)
Figure imgb0088
Figure imgb0089
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom in der Formel (I) bedeutet, oder
R2
f) für einen Rest aus der Reihe C1-C6-Halogenalkyl und Carboxyl steht, oder
R2
g) für einen Rest der Formel
Figure imgb0090
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, worin
G2
für Wasserstoff oder für einen Rest aus der Reihe Halogen, Nitro, Amino, Cyano, C1-C4-Alkylamino, Halogen-C1-C4-alkylamino, Di-(C1-C4-alkyl)-amino, C1-C4-Alkyl, Halogen-C1-C4-alkyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkenyl, C3-C6-Cycloalkyl-C1-C4-alkyl, C1-C4-Alkoxy, Halogen-C1-C4-alkoxy, C1-C4-Alkoxy-C1-C4-alkyl, halogeniertes C1-C4-Alkoxy-C1-C4-alkyl, Bis(C1-C4-alkoxy)-C1-C4-alkyl, Bis(halogen-C1-C4-alkoxy)-C1-C4-alkyl, C1-C4-Alkoxy-(C1-C4-alkylsulfanyl)-C1-C4-alkyl, C1-C4-Alkoxy-(C1-C4-alkylsulfinyl)-C1-C4-alkyl, C1-C4-Alkoxy-(C1-C4-alkylsulfonyl)-C1-C4-alkyl, Bis(C1-C4-alkylsulfanyl)-C1-C4-alkyl, Bis(halogen-C1-C4-alkylsulfanyl)-C1-C4-alkyl, Bis(hydroxy-C1-C4-alkylsulfanyl)-C1-C4-alkyl, C1-C4-Alkoxycarbonyl, C1-C4-Alkoxycarbonyl-C1-C4-alkyl, alpha-Hydroxyimino-C1-C4-alkoxycarbonyl-C1-C4-alkyl, alpha-C1-C4-Alkoxy-imino-C1-C4-alkoxycarbonyl-C1-C4-alkyl, C(X2)NR3R4, NR6R7, C1-C4-Alkylthio, C1-C4-Alkylsulfinyl, C1-C4-Alkylsulfonyl, C1-C4-Halogenalkylthio, C1-C4-Halogenalkylsulfinyl, C1-C4-Halogenalkylsulfonyl, die Heterocyclylreste Dioxanyl, Dioxolanyl, Dioxepanyl, Dioxocanyl, Oxathianyl, Oxathiolanyl, Oxathiepanyl, Oxathiocanyl, Dithianyl, Dithiolanyl, Dithiepanyl, Dithiocanyl, Oxathianyloxid, Oxathiolanyloxid, Oxathiepanyloxid, Oxathiocanyloxid, Oxathianyldioxid, Oxathiolanyldioxid, Oxathiepanyldioxid, Oxathiocanyldioxid, Morpholinyl, Triazolinonyl, Oxazolinyl, Dihydrooxadiazinyl, Dihydrodioxazinyl, Dihydrooxazolyl, Dihydrooxazinyl und Pyrazolinonyl (welche selbst wiederum substituiert sein können durch C1-C4-Alkyl, Halogen-C1-C4-alkyl, C1-C4-Alkoxy und C1-C4-Alkoxy-C1-C4-alkyl), Phenyl (welches selbst wiederum substituiert sein kann durch Halogen, Cyano, Nitro, C1-C4-Alkyl und Halogen-C1-C4-alkyl), die Heteroarylreste Pyridyl, Pyridyl-N-oxid, Pyrimidyl, Imidazolyl, Pyrazolyl, Oxazolyl, Thiazolyl, Furanyl, Thienyl, Triazolyl, Tetrazolyl, Oxadiazolyl, Thiadiazolyl, Pyrazinyl, Triazinyl, Tetrazinyl und Isochinolinyl (welche selbst wiederum substituiert sein können durch Halogen, Nitro, C1-C4-Alkyl, Halogen-C1-C4-alkyl, C1-C4-Alkoxy, Halogen-C1-C4-alkoxy, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4-Alkylthio, C1-C4-Alkylthio-C1-C4-alkyl und C3-C6-Cycloalkyl) und die Heteroaryl-C1-C4-alkylreste Triazolyl-C1-C4-alkyl, Pyridyl-C1-C4-alkyl, Pyrimidyl-C1-C4-alkyl und Oxadiazolyl-C1-C4-alkyl (welche selbst wiederum substituiert sein können durch Halogen und C1-C4-Alkyl) steht,
oder
G2
für einen C-Rest aus der Reihe (C-1) und (C-6) bis (C-9)
Figure imgb0091
Figure imgb0092
 steht, worin die gestrichelte Linie die Bindung zu den B-Resten bedeutet,
X
für Sauerstoff oder Schwefel steht,
X1
für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Nitro, C1-C6-Alkyl, C1-C6-Halogenalkyl, C3-C6-Cycloalkyl, C1-C6-Alkoxy und C1-C6-Halogenalkoxy steht,
X2
für Sauerstoff, Schwefel, NR5 oder NOH steht,
V-Z
für R24CH-CHR25 oder R24C=CR25 steht,
n
für 1 oder 2 steht,
R
für NR18R19 oder für jeweils gegebenfalls durch Halogen, Sauerstoff (führt zu C=O) oder Cyano substituiertes C1-C6-Alkyl, C3-C6-Alkenyl, C3-C6-Alkinyl, C1-C6-Alkoxy-C1-C4-alkyl, C1-C6-Alkyl-S-C1-C4-alkyl, C1-C6-Alkyl-S(O)-C1-C4-alkyl, C1-C6-Alkyl-S(O)2-C1-C4-alkyl, für R18-CO-C1-C4-alkyl, für NR18R19-CO-C1-C4-alkyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=O), C1-C4-Alkyl, C3-C8-Cycloalkyl, C1-C4-Alkoxy und C1-C4-Halogenalkyl substituiertes C3-C6-Cycloalkyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=O), C1-C4-Alkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy und C1-C4-Halogenalkyl substituiertes C3-C8-Cycloalkenyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=O), C1-C4-Alkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy und C1-C4-Halogenalkyl substituiertes C3-C6-Cycloalkyl-C1-C4-alkyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=O), C1-C4-Alkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy und C1-C4-Halogenalkyl substituiertes C3-C6-Cycloalkenyl-C1-C4-alkyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=O), C1-C4-Alkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy und C1-C4-Halogenalkyl substituiertes Heterocyclyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=O), C1-C4-Alkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy und C1-C4-Halogenalkyl substituiertes Heterocyclyl-C1-C4-alkyl oder für jeweils gegebenenfalls einfach bis dreifach durch Halogen, Cyano, C1-C4-Alkyl, C1-C4-Halogenalkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy oder C1-C4-Halogenalkoxy substituiertes Phenyl, Phenyl-C1-C4-alkyl, Hetaryl und Hetaryl-C1-C4-alkyl steht,
R3
für Wasserstoff oder C1-C6-Alkyl steht,
R4
für einen Rest aus der Reihe Wasserstoff, C1-C4-Alkyl, Halogen-C1-C4-alkyl, Cyano-C1-C4-alkyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C4-alkyl, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4-Alkoxycarbonyl, C1-C4-Alkoxycarbonyl-C1-C4-alkyl, C1-C4-Alkylthio-C1-C4-alkyl, Aryl, Aryl-C1-C4-alkyl und Hetaryl-C1-C4-alkyl steht,
R5
für einen Rest aus der Reihe Wasserstoff, C1-C4-Alkyl, Halogen- C1-C4-alkyl, Cyano-C1-C4-alkyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C4-alkyl, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4-Alkoxycarbonyl, C1-C4-Alkoxycarbonyl-C1-C4-alkyl, C1-C4-Alkylthio-C1-C4-alkyl, Aryl, Aryl-C1-C4-alkyl und Hetaryl-C1-C4-alkyl steht, oder
R3 und R4
gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen 4- bis 7-gliedrigen Ring bilden, der ein oder zwei weitere Heteroatome aus der Reihe Stickstoff, Sauerstoff und Schwefel (wobei Sauerstoff- und Schwefelatome nicht unmittelbar benachbart sein dürfen) enthalten kann,
R6
für Wasserstoff oder C1-C4-Alkyl steht,
R7
für einen Rest aus der Reihe Wasserstoff, C1-C4-Alkyl, Halogen-C1-C4-alkyl, Cyano-C1-C4-alkyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C4-Cycloalkyl-C1-C4-alkyl, C1-C4-Alkoxy, Halogen-C1-C4-alkoxy, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4-Alkoxycarbonyl, C1-C4-Alkoxycarbonyl-C1-C4-alkyl, C1-C4-Alkylthio-C1-C4-alkyl, Aryl, Aryl-C1-C4-alkyl oder Hetaryl-C1-C4-alkyl steht, oder
R6 und R7
gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen 4- bis 7-gliedrigen Ring bilden, der ein oder zwei weitere Heteroatome aus der Reihe Stickstoff, Sauerstoff und Schwefel (wobei Sauerstoff- und Schwefelatome nicht unmittelbar benachbart sein dürfen) enthalten kann,
R8
für einen Rest aus der Reihe Wasserstoff, C1-C6-Alkyl, C1-C6-Halogenalkyl, Cyano-C1-C6-alkyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C2-C6-Alkenyl, C1-C6-Alkoxy-C1-C6-alkyl, jeweils gegebenenfalls durch Halogen substituiertes C1-C6-Alkylcarbonyl und C1-C6-Alkylsulfonyl, gegebenenfalls durch Halogen substituiertes C1-C6-Alkoxycarbonyl und gegebenenfalls durch Halogen, C1-C6-Alkyl, C1-C6-Alkoxy, C1-C6-Halogenalkyl und Cyano substituiertes C3-C6-Cycloalkylcarbonyl steht, oder für ein Kation oder für ein gegebenenfalls durch C1-C6-Alkyl oder Aryl-C1-C6-alkyl substituiertes Ammonium-Ion steht,
R9
für einen Rest aus der Reihe jeweils gegebenenfalls durch Halogen, C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C1-C6-Alkylthio, C1-C6-Halogenalkylthio, C1-C6-Alkylsulfinyl, C1-C6-Halogenalkylsulfinyl, C1-C6-Alkylsulfonyl und C1-C6-Halogenalkylsulfonyl substituiertes C1-C6-Alkyl, C2-C6-Alkenyl und C2-C6-Alkinyl, jeweils gegebenenfalls durch Halogen, C1-C6-Alkyl, C1-C6-Halogenalkyl, C1-C6-Alkoxy oder C1-C6-Halogenalkoxy substituiertes C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C6-alkyl und C3-C6-Cycloalkenyl, in welchen ein Ringglied durch ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff ersetzt sein kann (und dabei insbesondere für
Figure imgb0093
 wobei der Pfeil jeweils die Bindung zum S-Atom im Rest (C-1) und im Rest (F-1) markiert), jeweils gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, C1-C6-Alkyl, C1-C6-Halogenalkyl, C3-C6-Cycloalkyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C1-C6-Alkylthio, C1-C6-Halogenalkylthio, C1-C6-Alkylsulfinyl, C1-C6-Halogenalkylsulfinyl, C1-C6-Alkylsulfonyl, C1-C6-Halogenalkylsulfonyl, Amino, C1-C6-Alkylamino, Di-(C1-C6-alkyl)-amino, C1-C6-Alkylcarbonylamino, C1-C6-Alkoxycarbonylamino, C1-C6-Alkoxy-C1-C6-alkyl, C1-C6-Halogenalkoxy-C1-C6-alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, C3-C6-Cycloalkyl-C1-C6-alkyl, C1-C6-Alkylcarbonyl, C1-C6-Alkoxycarbonyl oder Aminocarbonyl substituiertes Aryl, Heteroaryl, Aryl-C1-C6-alkyl, Heteroaryl-C1-C6-alkyl oder für NR'R" steht, worin R' und R" unabhängig voneinander für einen Rest aus der Reihe Wasserstoff, C1-C6-Alkyl, C1-C6-Halogenalkyl, C3-C6-Cycloalkyl, C1-C6-Alkoxy, C1-C6-Alkylcarbonyl und C1-C6-Alkoxylcarbonyl stehen, oder
R8 und R9
können im Rest (C-1) und im Rest (F-1) auch zusammen mit der N-S(O)n-Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls durch Halogen, C1-C6-Alkyl, C1-C6-Halogenalkyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy substituierten 5- bis 7-gliedrigen Ring bilden, der ein oder zwei Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine und bevorzugt eine Carbonylgruppe enthalten kann, insbesondere können R8 und R9 zusammen mit der N-S(O)n-Gruppe, an die sie gebunden sind, für einen Rest aus der Reihe
Figure imgb0094
Figure imgb0095
 stehen (worin der Pfeil jeweils die Bindung zur C(X)-Gruppe markiert),
R15
für einen Rest aus der Reihe jeweils gegebenenfalls durch Methyl, Cyano, Carbamoyl, substituiertes C1-C6-Alkyl, C2-C6-Alkenyl und C2-C6-Alkinyl, jeweils gegebenenfalls durch Methyl, Trifluormethyl, Halogen, Cyano oder Carbamoyl, substituiertes C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C2-alkyl und C3-C6-Cycloalkenyl, in welchen die Ringe mindestens ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff enthalten können, jeweils gegebenenfalls durch C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C1-C4-Alkylthio, C1-C4-Halogenalkylthio, C1-C4-Halogenalkylsulfinyl, C1-C4-Halogenalkylsulfonyl, C1-C4-Alkylamino, Di-(C1-C4-alkyl)-amino, Halogen, Nitro oder Cyano substituiertes Aryl, Heteroaryl, Aryl-C1-C4-alkyl und Heteroaryl-C1-C2-alkyl und eine gegebenenfalls durch C1-C4-Alkyl, C1-C4-Alkylcarbonyl, C1-C4-Alkyl-C1-C4-alkoxycarbonyl oder C1-C4-Alkylsulfonyl substituierte Aminogruppe steht,
R8 und R15
im Rest (C-6) auch zusammen mit der N-S(O)n-Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring bilden können, der ein oder zwei weitere Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoff- und Schwefelatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann,
R16
für einen Rest aus der Reihe Wasserstoff, jeweils gegebenenfalls durch Methyl, Cyano, Carbamoyl oder Carboxyl substituiertes C1-C6-Alkyl, C1-C6-Alkoxy, C2-C4-Alkenyl und C2-C4-Alkinyl, jeweils gegebenenfalls durch Halogen, Cyano, Nitro, C1-C6-Alkyl, C1-C6-Halogenalkyl, C3-C6-Cycloalkyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C1-C6-Alkylthio, C1-C6-Halogenalkylthio, C1-C6-Alkylsulfinyl, C1-C6-Halogenalkylsulfinyl, C1-C6-Alkylsulfonyl, C1-C6-Halogenalkylsulfonyl, Amino, C1-C6-Alkylamino, Di-(C1-C6-alkyl)-amino, C1-C6-Alkylcarbonylamino, C1-C6-Alkoxycarbonylamino, C2-C6-Alkenyl, C2-C6-Alkinyl oder C1-C6-Alkylcarbonyl substituiertes C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C4-alkyl und C3-C6-Cycloalkenyl, in welchen die Ringe mindestens ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff enthalten können, jeweils gegebenenfalls durch Halogen, Cyano, Nitro, C1-C6-Alkyl, C1-C6-Halogenalkyl, C3-C6-Cycloalkyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C1-C6-Alkylthio, C1-C6-Halogenalkylthio, C1-C6-Alkylsulfinyl, C1-C6-Halogenalkylsulfinyl, C1-C6-Alkylsulfonyl, C1-C6-Halogenalkylsulfonyl, Amino, C1-C6-Alkylamino, Di-(C1-C6-alkyl)-amino, C1-C6-Alkylcarbonylamino, C1-C6-Alkoxycarbonylamino, C2-C6-Alkenyl, C2-C6-Alkinyl oder C1-C6-Alkylcarbonyl substituiertes Aryl, Heteroaryl, Aryl-C1-C2-alkyl und Heteroaryl-C1-C2-alkyl und eine gegebenenfalls durch C1-C6-Alkyl, C1-C6-Halogenalkyl, C3-C6-Cycloalkyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C1-C6-Alkylthio, C1-C6-Halogenalkylthio, C1-C6-Alkylsulfinyl, C1-C6-Halogenalkylsulfinyl, C1-C6-Alkylsulfonyl, C1-C6-Halogenalkylsulfonyl, C2-C6-Alkenyl, C2-C6-Alkinyl oder C1-C6-Alkylcarbonyl substituierte Aminogruppe steht,
R17
für einen Rest aus der Reihe jeweils gegebenenfalls durch Halogen, C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C1-C6-Alkylthio, C1-C6-Halogenalkylthio, C1-C6-Alkylsulfinyl, C1-C6-Halogenalkylsulfinyl, C1-C6-Alkylsulfonyl oder C1-C6-Halogenalkylsulfonyl substituiertes C1-C6-Alkyl, C1-C6-Alkoxy, C2-C6-Alkenyl und C2-C6-Alkinyl, jeweils gegebenenfalls durch Halogen, C1-C6-Alkyl, C1-C6-Halogenalkyl, C1-C6-Alkoxy oder C1-C6-Halogenalkoxy substituiertes C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C6-alkyl, C3-C6-Cycloalkenyl, N-Pyrrolidinyl, N-Piperidinyl, N-Morpholinyl, N-Thiomorpholinyl, N-Thiomorpholinyl-1-oxid, N-Thiomorpholinyl-1,1-dioxid, N-Piperazinyl, N-1-Methylpiperazinyl und N-2-Oxo-1-methylpiperazinyl, jeweils gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, C1-C6-Alkyl, C1-C6-Halogenalkyl, C3-C6-Cycloalkyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C1-C6-Alkylthio, C1-C6-Halogenalkylthio, C1-C6-Alkylsulfinyl, C1-C6-Halogenalkylsulfinyl, C1-C6-Alkylsulfonyl, C1-C6-Halogenalkylsulfonyl, Amino, C1-C6-Alkylamino, Di-(C1-C6-alkyl)-amino, C1-C6-Alkylcarbonylamino, C1-C6-Alkoxycarbonylamino, C1-C6-Alkoxy-C1-C6-alkyl, C1-C6-Halogenalkoxy-C1-C6-alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, C3-C6-Cycloalkyl-C1-C6-alkyl, C1-C6-Alkylcarbonyl, C1-C6-Alkoxycarbonyl oder Aminocarbonyl substituiertes Aryl, Heteroaryl, Aryl-C1-C6-alkyl, Heteroaryl-C1-C6-alkyl und NR'R" steht, worin R' und R" unabhängig voneinander jeweils für einen Rest aus der Reihe Wasserstoff, C1-C6-Alkyl, C1-C6-Haloalkyl, C3-C6-Cycloalkyl, C1-C6-Alkoxy, C1-C6-Alkylcarbonyl und C1-C6-Alkoxylcarbonyl stehen,
R8 und R17
können im Rest (C-8) und im Rest (F-8) auch zusammen mit der N-C(X) Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls durch Halogen, C1-C6-Alkyl, C1-C6-Halogenalkyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy substituierten 5- bis 7-gliedrigen Ring bilden, der ein oder zwei weitere Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder eine Carbonylgruppe enthalten kann, insbesondere können R8 und R17 zusammen mit der N-C(X) Gruppe, an die sie gebunden sind, für einen Rest aus der Reihe
Figure imgb0096
Figure imgb0097
 stehen (worin der Pfeil jeweils die Bindung zum S-Atom im Rest (C-8) und im Rest (F-8) markiert),
R18
für einen Rest aus der Reihe Wasserstoff, Hydroxy, jeweils gegebenenfalls einfach oder mehrfach durch Halogen oder einfach oder zweifach durch Cyano substituiertes C1-C6-Alkyl, C1-C6-Alkoxy, C1-C6-Alkoxy-C1-C4-alkyl, C1-C6-Alkyl-S-C1-C4-alkyl, C1-C6-Alkyl-S(O)-C1-C4-alkyl, C1-C6-Alkyl-S(O)2-C1-C4-alkyl, C1-C6-Alkylcarbonyl, C1-C6-Alkoxycarbonyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkenyl, C3-C6-Cycloalkyl-C1-C3-alkyl, C3-C6-Cycloalkenyl-C1-C3-alkyl, Heterocyclyl, Heterocyclyl-C1-C3-alkyl und jeweils gegebenenfalls einfach bis vierfach durch C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C3-C6-Cycloalkyl, Halogen oder Cyano substituiertes Phenyl, Phenyl-C1-C3-alkyl, Hetaryl und Hetaryl-C1-C3-alkyl steht,
R19
für Wasserstoff, ein Alkali- oder Erdalkalimetallion oder für ein gegebenfalls einfach bis vierfach durch C1-C4-Alkyl substituiertes Ammoniumion oder für einen jeweils gegebenenfalls einfach oder mehrfach durch Halogen oder einfach oder zweifach durch Cyano substituierten Rest aus der Reihe C1-C4-Alkyl, C1-C4-Alkoxy, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4-Alkyl-S-C1-C4-alkyl, C1-C4-Alkyl-S(O)-C1-C4-alkyl und C1-C4-Alkyl-S(O)2-C1-C4-alkyl steht,
Y3
für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, C1-C6-Alkyl, C1-C6-Halogenalkyl, C3-C6-Cycloalkyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy und NR20R21 steht,
W
für einen Rest aus der Reihe O, S, SO und SO2 steht,
R22
für einen Rest aus der Reihe Wasserstoff, C1-C6-Alkyl, C2-C6-Halogenalkyl, Cyano-C1-C6-alkyl, C2-C4-Alkenyl, C2-C4-Halogenalkenyl, C2-C4-Alkinyl, C2-C4-Halogenalkinyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy, gegebenenfalls durch Halogen substituiertes C1-C6-Alkoxy-C1-C6-alkyl, gegebenenfalls durch Halogen substituiertes Bis(C1-C6-alkoxy)-C1-C6-alkyl, gegebenenfalls durch Halogen substituiertes C1-C6-Alkylsulfanyl-C1-C6-alkyl, gegebenenfalls durch Halogen substituiertes C1-C4-Alkylcarbonyl-C1-C4-alkyl, gegebenenfalls durch Halogen substituiertes C1-C6-Alkylsulfinyl-C1-C6-alkyl, gegebenenfalls durch Halogen substituiertes C1-C6-Alkylsulfonyl-C1-C6-alkyl, Di-(C1-C6-alkyl)-aminosulfanyl-C1-C6-alkyl, Di-(C1-C6-alkyl)-aminosulfinyl-C1-C6-alkyl, Di-(C1-C6-alkyl)-aminosulfonyl-C1-C6-alkyl, gegebenenfalls durch Halogen substituiertes C1-C6-Alkoxycarbonyl, gegebenenfalls durch Halogen substituiertes C1-C6-Alkoxycarbonyl-C1-C6-alkyl, gegebenenfalls durch Halogen substituiertes C2-C4-Alkinyloxy, gegebenenfalls durch Halogen substituiertes C2-C4-Alkinyloxycarbonyl, Di-(C1-C6-alkyl)-aminocarbonyl, N-C1-C6-Alkyl-N-C3-C6-cycloalkylaminocarbonyl, Di-(C1-C6-alkyl)-aminocarbonyl-C1-C6-alkyl, N-C1-C6-Alkyl-N-C3-C6-cycloalkylaminocarbonyl-C1-C6-alkyl, Heterocyclylcarbonyl-C1-C6-alkyl, C1-C6-Alkylsulfanyl, C1-C6-Halogenalkylsulfanyl, C1-C6-Alkylsulfinyl, C1-C6-Halogenalkylsulfinyl, C1-C6-Alkylsulfonyl, C1-C6-Halogenalkylsulfonyl, gegebenenfalls durch Halogen, Cyano, Nitro, C1-C6-Alkyl, C1-C6-Halogenalkyl, C3-C6-Cycloalkyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C1-C6-Alkoxycarbonyl, C1-C6-Halogenalkoxycarbonyl oder Hetaryl (welches gegebenenfalls selbst durch C1-C6-Alkyl oder Halogen substituiert ist) substituiertes C3-C6-Cycloalkyl, gegebenenfalls durch Halogen, Cyano, Nitro, C1-C6-Alkyl, C1-C6-Halogenalkyl, C3-C6-Cycloalkyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C1-C6-Alkoxycarbonyl, C1-C6-Halogenalkoxycarbonyl oder Hetaryl (welches gegebenenfalls selbst durch C1-C6-Alkyl oder Halogen substituiert ist) substituiertes C3-C6-Cycloalkylcarbonyl, gegebenenfalls durch Halogen, Cyano, Nitro, C1-C6-Alkyl, C1-C6-Halogenalkyl, C3-C6-Cycloalkyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C1-C6-Alkoxycarbonyl, C1-C6-Halogenalkoxycarbonyl oder Hetaryl (welches gegebenenfalls selbst durch C1-C6-Alkyl oder Halogen substituiert ist) substituiertes C3-C6-Cycloalkyl-C1-C6-alkyl, gegebenenfalls durch Halogen, Cyano (auch im C1-C6-Alkylteil von Heterocyclyl-C1-C6-alkyl), Nitro, Hydroxy, C1-C6-Alkyl, C1-C6-Halogenalkyl, C3-C6-Cycloalkyl (welches gegebenenfalls durch Halogen, Cyano, C1-C6-Alkyl und C3-C6-Cycloalkyl substituiert ist), C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C1-C6-Alkylthio, C1-C6-Halogenalkylthio, C1-C6-Alkylsulfinyl, C1-C6-Alkylsulfonyl, C1-C6-Halogenalkylsulfinyl, C1-C6-Halogenalkylsulfonyl, Amino, C1-C6-Alkylamino, Di-(C1-C6-alkyl)-amino, C1-C6-Alkylcarbonylamino, C1-C6-Alkoxycarbonylamino, C1-C6-Alkoxy-C1-C6-alkyl, C1-C6-Halogenalkoxy-C1-C6-alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, C3-C6-Cycloalkyl-C1-C6-alkyl, C1-C6-Alkylcarbonyl, C1-C6-Alkoxycarbonyl oder Aminocarbonyl substituiertes Heterocyclyl-C1-C6-alkyl, gegebenenfalls durch Halogen, Cyano, Nitro, Hydroxy, Amino, C1-C6-Alkyl, C1-C6-Halogenalkyl, C3-C6-Cycloalkyl (welches gegebenenfalls durch Halogen, Cyano, C1-C6-Alkyl und C3-C6-Cycloalkyl substituiert ist), C1-C6-Alkoxy oder C1-C6-Halogenalkoxy substituiertes Aryl, gegebenenfalls durch Halogen, Cyano (auch im C1-C6-Alkylteil von Aryl-C1-C6-alkyl), Nitro, Hydroxy, Amino, C1-C6-Alkyl, C1-C6-Halogenalkyl, C3-C6-Cycloalkyl (welches gegebenenfalls durch Halogen, Cyano, C1-C6-Alkyl und C3-C6-Cycloalkyl substituiert ist), C1-C6-Alkoxy oder C1-C6-Halogenalkoxy substituiertes Aryl-C1-C6-alkyl, gegebenenfalls durch Halogen, Cyano (auch im C1-C6-Alkylteil von Hetaryl-C1-C6-alkyl), Nitro, Hydroxy, C1-C6-Alkyl, C1-C6-Halogenalkyl, C3-C6-Cycloalkyl (welches gegebenenfalls durch Halogen, Cyano, C1-C6-Alkyl und C3-C6-Cycloalkyl substituiert ist), C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C1-C6-Alkylthio, C1-C6-Halogenalkylthio, C1-C6-Alkylsulfinyl, C1-C6-Alkylsulfonyl, C1-C6-Halogenalkylsulfinyl, C1-C6-Halogenalkylsulfonyl, Amino, C1-C6-Alkylamino, Di-(C1-C6-alkyl)-amino, C1-C6-Alkylcarbonylamino, C1-C6-Alkoxycarbonylamino, C1-C6-Alkoxy-C1-C6-alkyl, C1-C6-Halogenalkoxy-C1-C6-alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, C1-C6-Alkyl-C3-C6-cycloalkyl, C3-C6-Cycloalkyl-C1-C6-alkyl, C1-C6-Alkylcarbonyl, C1-C6-Alkoxycarbonyl oder Aminocarbonyl substituiertes Hetaryl-C1-C6-alkyl, oder
R22
für einen Rest aus der Reihe (D-1) bis (D-3)
Figure imgb0098
 aus der Reihe (E-1) bis (E-11)
Figure imgb0099
Figure imgb0100
Figure imgb0101
 und (E-18) bis (E-51)
Figure imgb0102
Figure imgb0103
Figure imgb0104
Figure imgb0105
Figure imgb0106
Figure imgb0107
Figure imgb0108
Figure imgb0109
Figure imgb0110
Figure imgb0111
 steht, oder
im Fall R2 = d),
R22
auch für einen E-Rest aus der Reihe E-12 bis E-17
Figure imgb0112
Figure imgb0113
 steht,
R20
für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Nitro, Amino, Hydroxy, C1-C6-Alkyl, C1-C6-Halogenalkyl, Cyano-C1-C6-alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, C3-C6-Cycloalkyl (welches gegebenenfalls durch Halogen, Cyano, C1-C4-Alkyl und C3-C6-Cycloalkyl substituiert ist), C3-C6-Cycloalkyl-C1-C6-alkyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C3-C6-Alkenyloxy, C3-C6-Alkinyloxy, C3-C6-Cycloalkyloxy, C1-C6-Alkylcarbonyloxy, C2-C6-Alkenylcarbonyloxy, C2-C6-Alkinylcarbonyloxy, C3-C6-Cycloalkylcarbonyloxy, C1-C6-Alkoxycarbonyloxy, C1-C6-Alkylsulfonyloxy, C1-C6-Alkylamino, C3-C6-Alkenylamino, C3-C6-Alkinylamino, C3-C6-Cycloalkylamino, C1-C6-Alkylthio, C1-C6-Halogenalkylthio, C3-C6-Alkenylthio, C3-C6-Alkinylthio, C3-C6-Cycloalkylthio, C1-C6-Alkylsulfinyl, C1-C6-Alkylsulfonyl, C1-C6-Alkylcarbonyl, C1-C6-Alkoxyimino-C1-C6-alkyl, C1-C6-Alkoxycarbonyl, Aminocarbonyl, C1-C6-Alkylaminocarbonyl, Di-(C1-C6-alkyl)-aminocarbonyl, Aminothiocarbonyl, C1-C6-Alkylaminosulfonyl, C1-C6-Alkylsulfonylamino, C1-C6-Alkylcarbonylamino, C1-C6-Alkylthiocarbonylamino, jeweils gegebenenfalls durch einen Rest aus der Reihe Halogen, Cyano, Nitro, Amino, Hydroxy, C1-C6-Alkyl oder C1-C6-Halogenalkyl substituiertes Phenyl, Phenoxy, Pyridinyl und Pyridinyloxy steht,
R21
für einen Rest aus der Reihe Wasserstoff, C1-C6-Alkyl, C3-C6-Cycloalkyl, C1-C6-Halogenalkyl, C3-C6-Alkenyl, C2-C6-Alkinyl, C3-C6-Cycloalkyl-C1-C6-alkyl, Cyano-C1-C6-alkyl, C1-C6-Alkylcarbonyl, C2-C6-Alkenylcarbonyl, C1-C6-Halogenalkylcarbonyl, C2-C6-Halogenalkenylcarbonyl, C1-C6-Alkoxy-C1-C6-alkyl, C1-C6-Alkoxycarbonyl, C1-C6-Alkylsulfonyl und C1-C6-Halogengenalkylsulfonyl steht,
R23
für einen Rest aus der Reihe Wasserstoff, C1-C6-Alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkenyl, C1-C6-Alkoxy, C2-C6-Alkenyloxy, C2-C6-Alkinyloxy, C3-C6-Cycloalkyloxy, C1-C4-Alkylthio-C1-C4-alkyl, C2-C4-Alkenylthio-C1-C4-alkyl, Cyano-C1-C4-alkyl, C1-C4-Alkoxy-C1-C4-alkyl steht,
oder, für R2 = c) oder g),
R22 und R23
gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen gesättigten Ring bilden, der ein oder mehrere weitere Heteroatome aus der Reihe Stickstoff, Sauerstoff und Schwefel enthalten kann, und
R24
für Wasserstoff oder einen jeweils gegebenenfalls durch Halogen oder Cyano substituierten Rest aus der Reihe C1-C4-Alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, Phenyl und Phenyl-C1-C2-alkyl steht,
R25
für Wasserstoff oder einen jeweils gegebenenfalls durch Halogen oder Cyano substituierten Rest aus der Reihe C1-C4-Alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, Phenyl und Phenyl-C1-C2-alkyl steht,
R26
für einen Rest aus der Reihe Wasserstoff, C1-C4-Alkyl, C1-C4-Halogenalkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C4-alkyl, C1-C4-Alkoxy-C1-C2-alkyl, C1-C6-Alkylsulfanyl, C1-C6-Halogenalkylsulfanyl C1-C6-Alkylsulfinyl, C1-C6-Halogenalkylsulfinyl, C1-C6-Alkylsulfonyl, C1-C4-Alkylthio-C1-C2-alkyl, C1-C4-Alkylsulfinyl-C1-C2-alkyl, C1-C4-Alkylsulfonyl-C1-C2-alkyl und Cyano-C1-C4-alkyl steht und
R27
für Wasserstoff, C1-C4-Alkyl, C1-C4-Halogenalkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C4-alkyl, C1-C4-Alkoxy-C1-C2-alkyl, C1-C4-Alkylthio-C1-C2-alkyl, C1-C4-Alkylsulfinyl-C1-C2-alkyl, C1-C4-Alkylsulfonyl-C1-C2-alkyl oder Cyano-C1-C4-alkyl steht und
Verbindungen der Formel (I), in welchen
A
für den A-Rest
Figure imgb0114
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, und
G1
für N oder C-B1 steht,
B1
für einen Rest aus der Reihe Wasserstoff, Halogen, C1-C6-Alkyl und C1-C4-Halogenalkyl steht,
B2
für einen Rest aus der Reihe Wasserstoff, Halogen, C1-C6-Alkyl und C1-C4-Halogenalkyl steht,
T
für Sauerstoff oder ein Elektronenpaar steht,
Q
für Schwefel steht,
R1
für einen Rest aus der Reihe Wasserstoff, C1-C6-Alkyl und C1-C6-Alkoxy steht,
R2
a) für einen B-Rest aus der Reihe
Figure imgb0115
Figure imgb0116
Figure imgb0117
Figure imgb0118
Figure imgb0119
Figure imgb0120
Figure imgb0121
Figure imgb0122
Figure imgb0123
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder
R2
c) für einen Rest der Formel
Figure imgb0124
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder
R2
d) für einen Rest der Formel
Figure imgb0125
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder
R2
e) für einen F-Rest aus der Reihe (F-8), (F-10) und (F-11)
Figure imgb0126
Figure imgb0127
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom in der Formel (I) bedeutet, oder
R2
f) für einen Rest aus der Reihe C1-C6-Halogenalkyl und Carboxyl steht, oder
R2
g) für einen Rest der Formel
Figure imgb0128
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, worin
G2
für Wasserstoff oder für einen Rest aus der Reihe Halogen, Nitro, Amino, Cyano, C1-C4-Alkylamino, Halogen-C1-C4-alkylamino, Di-(C1-C4-alkyl)-amino, C1-C4-Alkyl, Halogen-C1-C4-alkyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkenyl, C3-C6-Cycloalkyl-C1-C4-alkyl, C1-C4-Alkoxy, Halogen-C1-C4-alkoxy, C1-C4-Alkoxy-C1-C4-alkyl, halogeniertes C1-C4-Alkoxy-C1-C4-alkyl, Bis(C1-C4-alkoxy)-C1-C4-alkyl, Bis(halogen-C1-C4-alkoxy)-C1-C4-alkyl, C1-C4-Alkoxy-(C1-C4-alkylsulfanyl)-C1-C4-alkyl, C1-C4-Alkoxy-(C1-C4-alkylsulfinyl)-C1-C4-alkyl, C1-C4-Alkoxy-(C1-C4-alkylsulfonyl)-C1-C4-alkyl, Bis(C1-C4-alkylsulfanyl)-C1-C4-alkyl, Bis(halogen-C1-C4-alkylsulfanyl)-C1-C4-alkyl, Bis(hydroxy-C1-C4-alkylsulfanyl)-C1-C4-alkyl, C1-C4-Alkoxycarbonyl, C1-C4-Alkoxycarbonyl-C1-C4-alkyl, alpha-Hydroxyimino-C1-C4-alkoxycarbonyl-C1-C4-alkyl, alpha-C1-C4-Alkoxy-imino-C1-C4-alkoxycarbonyl-C1-C4-alkyl, C(X2)NR3R4, NR6R7, C1-C4-Alkylthio, C1-C4-Alkylsulfinyl, C1-C4-Alkylsulfonyl, C1-C4-Halogenalkylthio, C1-C4-Halogenalkylsulfinyl, C1-C4-Halogenalkylsulfonyl, die Heterocyclylreste Dioxanyl, Dioxolanyl, Dioxepanyl, Dioxocanyl, Oxathianyl, Oxathiolanyl, Oxathiepanyl, Oxathiocanyl, Dithianyl, Dithiolanyl, Dithiepanyl, Dithiocanyl, Oxathianyloxid, Oxathiolanyloxid, Oxathiepanyloxid, Oxathiocanyloxid, Oxathianyldioxid, Oxathiolanyldioxid, Oxathiepanyldioxid, Oxathiocanyldioxid, Morpholinyl, Triazolinonyl, Oxazolinyl, Dihydrooxadiazinyl, Dihydrodioxazinyl, Dihydrooxazolyl, Dihydrooxazinyl und Pyrazolinonyl (welche selbst wiederum substituiert sein können durch C1-C4-Alkyl, Halogen-C1-C4-alkyl, C1-C4-Alkoxy und C1-C4-Alkoxy-C1-C4-alkyl), Phenyl (welches selbst wiederum substituiert sein kann durch Halogen, Cyano, Nitro, C1-C4-Alkyl und Halogen-C1-C4-alkyl), die Heteroarylreste Pyridyl, Pyridyl-N-oxid, Pyrimidyl, Imidazolyl, Pyrazolyl, Oxazolyl, Thiazolyl, Furanyl, Thienyl, Triazolyl, Tetrazolyl, Oxadiazolyl, Thiadiazolyl, Pyrazinyl, Triazinyl, Tetrazinyl und Isochinolinyl (welche selbst wiederum substituiert sein können durch Halogen, Nitro, C1-C4-Alkyl, Halogen-C1-C4-alkyl, C1-C4-Alkoxy, Halogen-C1-C4-alkoxy, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4-Alkylthio, C1-C4-Alkylthio-C1-C4-alkyl und C3-C6-Cycloalkyl) und die Heteroaryl-C1-C4-alkylreste Triazolyl-C1-C4-alkyl, Pyridyl-C1-C4-alkyl, Pyrimidyl-C1-C4-alkyl und Oxadiazolyl-C1-C4-alkyl (welche selbst wiederum substituiert sein können durch Halogen und C1-C4-Alkyl) steht, oder
G2
für einen C-Rest aus der Reihe (C-1) und (C-6) bis (C-9)
Figure imgb0129
Figure imgb0130
 steht, worin die gestrichelte Linie die Bindung zu den B-Resten bedeutet,
X
für Sauerstoff oder Schwefel steht,
X2
für Sauerstoff, Schwefel, NR5 oder NOH steht,
V-Z
für R24CH-CHR25 oder R24C=CR25 steht,
n
für 1 oder 2 steht,
R3
für Wasserstoff oder C1-C6-Alkyl steht,
R4
für einen Rest aus der Reihe Wasserstoff, C1-C4-Alkyl, Halogen-C1-C4-alkyl, Cyano-C1-C4-alkyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C4-alkyl, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4-Alkoxycarbonyl, C1-C4-Alkoxycarbonyl-C1-C4-alkyl, C1-C4-Alkylthio-C1-C4-alkyl, Aryl, Aryl-C1-C4-alkyl und Hetaryl-C1-C4-alkyl steht,
R5
für einen Rest aus der Reihe Wasserstoff, C1-C4-Alkyl, Halogen- C1-C4-alkyl, Cyano-C1-C4-alkyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C4-alkyl, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4-Alkoxycarbonyl, C1-C4-Alkoxycarbonyl-C1-C4-alkyl, C1-C4-Alkylthio-C1-C4-alkyl, Aryl, Aryl-C1-C4-alkyl und Hetaryl-C1-C4-alkyl steht, oder
R3 und R4
gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen 4- bis 7-gliedrigen Ring bilden, der ein oder zwei weitere Heteroatome aus der Reihe Stickstoff, Sauerstoff und Schwefel (wobei Sauerstoff- und Schwefelatome nicht unmittelbar benachbart sein dürfen) enthalten kann,
R6
für Wasserstoff oder C1-C4-Alkyl steht,
R7
für einen Rest aus der Reihe Wasserstoff, C1-C4-Alkyl, Halogen-C1-C4-alkyl, Cyano-C1-C4-alkyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C4-Cycloalkyl-C1-C4-alkyl, C1-C4-Alkoxy, Halogen-C1-C4-alkoxy, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4-Alkoxycarbonyl, C1-C4-Alkoxycarbonyl-C1-C4-alkyl, C1-C4-Alkylthio-C1-C4-alkyl, Aryl, Aryl-C1-C4-alkyl oder Hetaryl-C1-C4-alkyl steht, oder
R6 und R7
gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen 4- bis 7-gliedrigen Ring bilden, der ein oder zwei weitere Heteroatome aus der Reihe Stickstoff, Sauerstoff und Schwefel (wobei Sauerstoff- und Schwefelatome nicht unmittelbar benachbart sein dürfen) enthalten kann,
R8
für einen Rest aus der Reihe Wasserstoff, C1-C6-Alkyl, C1-C6-Halogenalkyl, Cyano-C1-C6-alkyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C2-C6-Alkenyl, C1-C6-Alkoxy-C1-C6-alkyl, jeweils gegebenenfalls durch Halogen substituiertes C1-C6-Alkylcarbonyl und C1-C6-Alkylsulfonyl, gegebenenfalls durch Halogen substituiertes C1-C6-Alkoxycarbonyl und gegebenenfalls durch Halogen, C1-C6-Alkyl, C1-C6-Alkoxy, C1-C6-Halogenalkyl und Cyano substituiertes C3-C6-Cycloalkylcarbonyl steht, oder für ein Kation oder für ein gegebenenfalls durch C1-C6-Alkyl oder Aryl-C1-C6-alkyl substituiertes Ammonium-Ion steht,
R9
für einen Rest aus der Reihe jeweils gegebenenfalls durch Halogen, C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C1-C6-Alkylthio, C1-C6-Halogenalkylthio, C1-C6-Alkylsulfinyl, C1-C6-Halogenalkylsulfinyl, C1-C6-Alkylsulfonyl und C1-C6-Halogenalkylsulfonyl substituiertes C1-C6-Alkyl, C2-C6-Alkenyl und C2-C6-Alkinyl, jeweils gegebenenfalls durch Halogen, C1-C6-Alkyl, C1-C6-Halogenalkyl, C1-C6-Alkoxy oder C1-C6-Halogenalkoxy substituiertes C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C6-alkyl und C3-C6-Cycloalkenyl, in welchen ein Ringglied durch ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff ersetzt sein kann (und dabei insbesondere für
Figure imgb0131
 wobei der Pfeil jeweils die Bindung zum S-Atom im Rest (C-1) und im Rest (F-1) markiert), jeweils gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, C1-C6-Alkyl, C1-C6-Halogenalkyl, C3-C6-Cycloalkyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C1-C6-Alkylthio, C1-C6-Halogenalkylthio, C1-C6-Alkylsulfinyl, C1-C6-Halogenalkylsulfinyl, C1-C6-Alkylsulfonyl, C1-C6-Halogenalkylsulfonyl, Amino, C1-C6-Alkylamino, Di-(C1-C6-alkyl)-amino, C1-C6-Alkylcarbonylamino, C1-C6-Alkoxycarbonylamino, C1-C6-Alkoxy-C1-C6-alkyl, C1-C6-Halogenalkoxy-C1-C6-alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, C3-C6-Cycloalkyl-C1-C6-alkyl, C1-C6-Alkylcarbonyl, C1-C6-Alkoxycarbonyl oder Aminocarbonyl substituiertes Aryl, Heteroaryl, Aryl-C1-C6-alkyl, Heteroaryl-C1-C6-alkyl oder für NR'R" steht, worin R' und R" unabhängig voneinander für einen Rest aus der Reihe Wasserstoff, C1-C6-Alkyl, C1-C6-Halogenalkyl, C3-C6-Cycloalkyl, C1-C6-Alkoxy, C1-C6-Alkylcarbonyl und C1-C6-Alkoxylcarbonyl stehen, oder
R8 und R9
können im Rest (C-1) auch zusammen mit der N-S(O)n-Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls durch Halogen, C1-C6-Alkyl, C1-C6-Halogenalkyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy substituierten 5- bis 7-gliedrigen Ring bilden, der ein oder zwei Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine und bevorzugt eine Carbonylgruppe enthalten kann, insbesondere können R8 und R9 zusammen mit der N-S(O)n-Gruppe, an die sie gebunden sind, für einen Rest aus der Reihe
Figure imgb0132
Figure imgb0133
 stehen (worin der Pfeil jeweils die Bindung zur C(X)-Gruppe markiert),
R15
für einen Rest aus der Reihe jeweils gegebenenfalls durch Methyl, Cyano, Carbamoyl, substituiertes C1-C6-Alkyl, C2-C6-Alkenyl und C2-C6-Alkinyl, jeweils gegebenenfalls durch Methyl, Trifluormethyl, Halogen, Cyano oder Carbamoyl, substituiertes C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C2-alkyl und C3-C6-Cycloalkenyl, in welchen die Ringe mindestens ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff enthalten können, jeweils gegebenenfalls durch C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C1-C4-Alkylthio, C1-C4-Halogenalkylthio, C1-C4-Halogenalkylsulfinyl, C1-C4-Halogenalkylsulfonyl, C1-C4-Alkylamino, Di-(C1-C4-alkyl)-amino, Halogen, Nitro oder Cyano substituiertes Aryl, Heteroaryl, Aryl-C1-C4-alkyl und Heteroaryl-C1-C2-alkyl und eine gegebenenfalls durch C1-C4-Alkyl, C1-C4-Alkylcarbonyl, C1-C4-Alkyl-C1-C4-alkoxycarbonyl oder C1-C4-Alkylsulfonyl substituierte Aminogruppe steht,
R8 und R15
im Rest (C-6) auch zusammen mit der N-S(O)n-Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring bilden können, der ein oder zwei weitere Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoff- und Schwefelatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann,
R16
für einen Rest aus der Reihe Wasserstoff, jeweils gegebenenfalls durch Methyl, Cyano, Carbamoyl oder Carboxyl substituiertes C1-C6-Alkyl, C1-C6-Alkoxy, C2-C4-Alkenyl und C2-C4-Alkinyl, jeweils gegebenenfalls durch Halogen, Cyano, Nitro, C1-C6-Alkyl, C1-C6-Halogenalkyl, C3-C6-Cycloalkyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C1-C6-Alkylthio, C1-C6-Halogenalkylthio, C1-C6-Alkylsulfinyl, C1-C6-Halogenalkylsulfinyl, C1-C6-Alkylsulfonyl, C1-C6-Halogenalkylsulfonyl, Amino, C1-C6-Alkylamino, Di-(C1-C6-alkyl)-amino, C1-C6-Alkylcarbonylamino, C1-C6-Alkoxycarbonylamino, C2-C6-Alkenyl, C2-C6-Alkinyl oder C1-C6-Alkylcarbonyl substituiertes C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C4-alkyl und C3-C6-Cycloalkenyl, in welchen die Ringe mindestens ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff enthalten können, jeweils gegebenenfalls durch Halogen, Cyano, Nitro, C1-C6-Alkyl, C1-C6-Halogenalkyl, C3-C6-Cycloalkyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C1-C6-Alkylthio, C1-C6-Halogenalkylthio, C1-C6-Alkylsulfinyl, C1-C6-Halogenalkylsulfinyl, C1-C6-Alkylsulfonyl, C1-C6-Halogenalkylsulfonyl, Amino, C1-C6-Alkylamino, Di-(C1-C6-alkyl)-amino, C1-C6-Alkylcarbonylamino, C1-C6-Alkoxycarbonylamino, C2-C6-Alkenyl, C2-C6-Alkinyl oder C1-C6-Alkylcarbonyl substituiertes Aryl, Heteroaryl, Aryl-C1-C2-alkyl und Heteroaryl-C1-C2-alkyl und eine gegebenenfalls durch C1-C6-Alkyl, C1-C6-Halogenalkyl, C3-C6-Cycloalkyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C1-C6-Alkylthio, C1-C6-Halogenalkylthio, C1-C6-Alkylsulfinyl, C1-C6-Halogenalkylsulfinyl, C1-C6-Alkylsulfonyl, C1-C6-Halogenalkylsulfonyl, C2-C6-Alkenyl, C2-C6-Alkinyl oder C1-C6-Alkylcarbonyl substituierte Aminogruppe steht,
R17
für einen Rest aus der Reihe jeweils gegebenenfalls durch Halogen, C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C1-C6-Alkylthio, C1-C6-Halogenalkylthio, C1-C6-Alkylsulfinyl, C1-C6-Halogenalkylsulfinyl, C1-C6-Alkylsulfonyl oder C1-C6-Halogenalkylsulfonyl substituiertes C1-C6-Alkyl, C1-C6-Alkoxy, C2-C6-Alkenyl und C2-C6-Alkinyl, jeweils gegebenenfalls durch Halogen, C1-C6-Alkyl, C1-C6-Halogenalkyl, C1-C6-Alkoxy oder C1-C6-Halogenalkoxy substituiertes C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C6-alkyl, C3-C6-Cycloalkenyl, N-Pyrrolidinyl, N-Piperidinyl, N-Morpholinyl, N-Thiomorpholinyl, N-Thiomorpholinyl-1-oxid, N-Thiomorpholinyl-1,1-dioxid, N-Piperazinyl, N-1-Methylpiperazinyl und N-2-Oxo-1-methylpiperazinyl, jeweils gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, C1-C6-Alkyl, C1-C6-Halogenalkyl, C3-C6-Cycloalkyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C1-C6-Alkylthio, C1-C6-Halogenalkylthio, C1-C6-Alkylsulfinyl, C1-C6-Halogenalkylsulfinyl, C1-C6-Alkylsulfonyl, C1-C6-Halogenalkylsulfonyl, Amino, C1-C6-Alkylamino, Di-(C1-C6-alkyl)-amino, C1-C6-Alkylcarbonylamino, C1-C6-Alkoxycarbonylamino, C1-C6-Alkoxy-C1-C6-alkyl, C1-C6-Halogenalkoxy-C1-C6-alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, C3-C6-Cycloalkyl-C1-C6-alkyl, C1-C6-Alkylcarbonyl, C1-C6-Alkoxycarbonyl oder Aminocarbonyl substituiertes Aryl, Heteroaryl, Aryl-C1-C6-alkyl, Heteroaryl-C1-C6-alkyl und NR'R" steht, worin R' und R" unabhängig voneinander jeweils für einen Rest aus der Reihe Wasserstoff, C1-C6-Alkyl, C1-C6-Haloalkyl, C3-C6-Cycloalkyl, C1-C6-Alkoxy, C1-C6-Alkylcarbonyl und C1-C6-Alkoxylcarbonyl stehen,
R8 und R17
können im Rest (C-8) und im Rest (F-8) auch zusammen mit der N-C(X) Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls durch Halogen, C1-C6-Alkyl, C1-C6-Halogenalkyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy substituierten 5- bis 7-gliedrigen Ring bilden, der ein oder zwei weitere Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder eine Carbonylgruppe enthalten kann, insbesondere können R8 und R17 zusammen mit der N-C(X) Gruppe, an die sie gebunden sind, für einen Rest aus der Reihe
Figure imgb0134
Figure imgb0135
 stehen (worin der Pfeil jeweils die Bindung zum S-Atom im Rest (C-8) und im Rest (F-8) markiert),
und im Fall, dass R2 für g) steht,
R22
für einen Rest aus der Reihe Wasserstoff, C1-C6-Alkyl, C2-C6-Halogenalkyl, Cyano-C1-C6-alkyl, C2-C4-Alkenyl, C2-C4-Halogenalkenyl, C2-C4-Alkinyl, C2-C4-Halogenalkinyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy, gegebenenfalls durch Halogen substituiertes C1-C6-Alkoxy-C1-C6-alkyl, gegebenenfalls durch Halogen substituiertes Bis(C1-C6-alkoxy)-C1-C6-alkyl, gegebenenfalls durch Halogen substituiertes C1-C6-Alkylsulfanyl-C1-C6-alkyl, gegebenenfalls durch Halogen substituiertes C1-C4-Alkylcarbonyl-C1-C4-alkyl, gegebenenfalls durch Halogen substituiertes C1-C6-Alkylsulfinyl-C1-C6-alkyl, gegebenenfalls durch Halogen substituiertes C1-C6-Alkylsulfonyl-C1-C6-alkyl, Di-(C1-C6-alkyl)-aminosulfanyl-C1-C6-alkyl, Di-(C1-C6-alkyl)-aminosulfinyl-C1-C6-alkyl, Di-(C1-C6-alkyl)-aminosulfonyl-C1-C6-alkyl, gegebenenfalls durch Halogen substituiertes C1-C6-Alkoxycarbonyl-C1-C6-alkyl, gegebenenfalls durch Halogen substituiertes C2-C4-Alkinyloxy, Di-(C1-C6-alkyl)-aminocarbonyl-C1-C6-alkyl, N-C1-C6-Alkyl-N-C3-C6-cycloalkylaminocarbonyl-C1-C6-alkyl, Heterocyclylcarbonyl-C1-C6-alkyl, C1-C6-Alkylsulfanyl, C1-C6-Halogenalkylsulfanyl, C1-C6-Alkylsulfinyl, C1-C6-Halogenalkylsulfinyl, C1-C6-Alkylsulfonyl, C1-C6-Halogenalkylsulfonyl, gegebenenfalls durch Halogen, Cyano, Nitro, C1-C6-Alkyl, C1-C6-Halogenalkyl, C3-C6-Cycloalkyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C1-C6-Alkoxycarbonyl, C1-C6-Halogenalkoxycarbonyl oder Hetaryl (welches gegebenenfalls selbst durch C1-C6-Alkyl oder Halogen substituiert ist) substituiertes C3-C6-Cycloalkyl, gegebenenfalls durch Halogen, Cyano, Nitro, C1-C6-Alkyl, C1-C6-Halogenalkyl, C3-C6-Cycloalkyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C1-C6-Alkoxycarbonyl, C1-C6-Halogenalkoxycarbonyl oder Hetaryl (welches gegebenenfalls selbst durch C1-C6-Alkyl oder Halogen substituiert ist) substituiertes C3-C6-Cycloalkyl-C1-C6-alkyl, gegebenenfalls durch Halogen, Cyano (auch im C1-C6-Alkylteil von Heterocyclyl-C1-C6-alkyl), Nitro, Hydroxy, C1-C6-Alkyl, C1-C6-Halogenalkyl, C3-C6-Cycloalkyl (welches gegebenenfalls durch Halogen, Cyano, C1-C6-Alkyl und C3-C6-Cycloalkyl substituiert ist), C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C1-C6-Alkylthio, C1-C6-Halogenalkylthio, C1-C6-Alkylsulfinyl, C1-C6-Alkylsulfonyl, C1-C6-Halogenalkylsulfinyl, C1-C6-Halogenalkylsulfonyl, Amino, C1-C6-Alkylamino, Di-(C1-C6-alkyl)-amino, C1-C6-Alkylcarbonylamino, C1-C6-Alkoxycarbonylamino, C1-C6-Alkoxy-C1-C6-alkyl, C1-C6-Halogenalkoxy-C1-C6-alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, C3-C6-Cycloalkyl-C1-C6-alkyl, C1-C6-Alkylcarbonyl, C1-C6-Alkoxycarbonyl oder Aminocarbonyl substituiertes Heterocyclyl-C1-C6-alkyl, gegebenenfalls durch Halogen, Cyano, Nitro, Hydroxy, Amino, C1-C6-Alkyl, C1-C6-Halogenalkyl, C3-C6-Cycloalkyl (welches gegebenenfalls durch Halogen, Cyano, C1-C6-Alkyl und C3-C6-Cycloalkyl substituiert ist), C1-C6-Alkoxy oder C1-C6-Halogenalkoxy substituiertes Aryl, gegebenenfalls durch Halogen, Cyano (auch im C1-C6-Alkylteil von Aryl-C1-C6-alkyl), Nitro, Hydroxy, Amino, C1-C6-Alkyl, C1-C6-Halogenalkyl, C3-C6-Cycloalkyl (welches gegebenenfalls durch Halogen, Cyano, C1-C6-Alkyl und C3-C6-Cycloalkyl substituiert ist), C1-C6-Alkoxy oder C1-C6-Halogenalkoxy substituiertes Aryl-C1-C6-alkyl, gegebenenfalls durch Halogen, Cyano (auch im C1-C6-Alkylteil von Hetaryl-C1-C6-alkyl), Nitro, Hydroxy, C1-C6-Alkyl, C1-C6-Halogenalkyl, C3-C6-Cycloalkyl (welches gegebenenfalls durch Halogen, Cyano, C1-C6-Alkyl und C3-C6-Cycloalkyl substituiert ist), C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C1-C6-Alkylthio, C1-C6-Halogenalkylthio, C1-C6-Alkylsulfinyl, C1-C6-Alkylsulfonyl, C1-C6-Halogenalkylsulfinyl, C1-C6-Halogenalkylsulfonyl, Amino, C1-C6-Alkylamino, Di-(C1-C6-alkyl)-amino, C1-C6-Alkylcarbonylamino, C1-C6-Alkoxycarbonylamino, C1-C6-Alkoxy-C1-C6-alkyl, C1-C6-Halogenalkoxy-C1-C6-alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, C1-C6-Alkyl-C3-C6-cycloalkyl, C3-C6-Cycloalkyl-C1-C6-alkyl, C1-C6-Alkylcarbonyl, C1-C6-Alkoxycarbonyl oder Aminocarbonyl substituiertes Hetaryl-C1-C6-alkyl, und im Fall, dass R2 für c), d) oder g) steht,
R22
für einen Rest aus der Reihe (D-1) bis (D-3)
Figure imgb0136
 worin
X1
für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Nitro, C1-C6-Alkyl, C1-C6-Halogenalkyl, C3-C6-Cycloalkyl, C1-C6-Alkoxy und C1-C6-Halogenalkoxy steht,
R
für NR18R19 oder für jeweils gegebenfalls durch Halogen, Sauerstoff (führt zu C=O) oder Cyano substituiertes C1-C6-Alkyl, C3-C6-Alkenyl, C3-C6-Alkinyl, C1-C6-Alkoxy-C1-C4-alkyl, C1-C6-Alkyl-S-C1-C4-alkyl, C1-C6-Alkyl-S(O)-C1-C4-alkyl, C1-C6-Alkyl-S(O)2-C1-C4-alkyl, für R18-CO-C1-C4-alkyl, für NR18R19-CO-C1-C4-alkyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=O), C1-C4-Alkyl, C3-C8-Cycloalkyl, C1-C4-Alkoxy und C1-C4-Halogenalkyl substituiertes C3-C6-Cycloalkyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=O), C1-C4-Alkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy und C1-C4-Halogenalkyl substituiertes C3-C8-Cycloalkenyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=O), C1-C4-Alkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy und C1-C4-Halogenalkyl substituiertes C3-C6-Cycloalkyl-C1-C4-alkyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=O), C1-C4-Alkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy und C1-C4-Halogenalkyl substituiertes C3-C6-Cycloalkenyl-C1-C4-alkyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=O), C1-C4-Alkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy und C1-C4-Halogenalkyl substituiertes Heterocyclyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=O), C1-C4-Alkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy und C1-C4-Halogenalkyl substituiertes Heterocyclyl-Ci-C4-alkyl oder für jeweils gegebenenfalls einfach bis dreifach durch Halogen, Cyano, C1-C4-Alkyl, C1-C4-Halogenalkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy oder C1-C4-Halogenalkoxy substituiertes Phenyl, Phenyl-C1-C4-alkyl, Hetaryl und Hetaryl-C1-C4-alkyl steht,
Y3
für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, C1-C6-Alkyl, C1-C6-Halogenalkyl, C3-C6-Cycloalkyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy undNR20R21 steht,
W
für einen Rest aus der Reihe O, S, SO und SO2 steht,
R22
ferner für einen Rest aus der Reihe (E-1) bis (E-11)
Figure imgb0137
Figure imgb0138
Figure imgb0139
 und (E-18) bis (E-51)
Figure imgb0140
Figure imgb0141
Figure imgb0142
Figure imgb0143
Figure imgb0144
Figure imgb0145
Figure imgb0146
Figure imgb0147
Figure imgb0148
Figure imgb0149
 steht, oder
im Fall R2 = d),
R22
auch für einen E-Rest aus der Reihe E-12 bis E-17
Figure imgb0150
Figure imgb0151
 steht,
R18
für einen Rest aus der Reihe Wasserstoff, Hydroxy, jeweils gegebenenfalls einfach oder mehrfach durch Halogen oder einfach oder zweifach durch Cyano substituiertes C1-C6-Alkyl, C1-C6-Alkoxy, C1-C6-Alkoxy-C1-C4-alkyl, C1-C6-Alkyl-S-C1-C4-alkyl, C1-C6-Alkyl-S(O)-C1-C4-alkyl, C1-C6-Alkyl-S(O)2-C1-C4-alkyl, C1-C6-Alkylcarbonyl, C1-C6-Alkoxycarbonyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkenyl, C3-C6-Cycloalkyl-C1-C3-alkyl, C3-C6-Cycloalkenyl-C1-C3-alkyl, Heterocyclyl, Heterocyclyl-C1-C3-alkyl und jeweils gegebenenfalls einfach bis vierfach durch C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C3-C6-Cycloalkyl, Halogen oder Cyano substituiertes Phenyl, Phenyl-C1-C3-alkyl, Hetaryl und Hetaryl-C1-C3-alkyl steht,
R19
für Wasserstoff, ein Alkali- oder Erdalkalimetallion oder für ein gegebenfalls einfach bis vierfach durch C1-C4-Alkyl substituiertes Ammoniumion oder für einen jeweils gegebenenfalls einfach oder mehrfach durch Halogen oder einfach oder zweifach durch Cyano substituierten Rest aus der Reihe C1-C4-Alkyl, C1-C4-Alkoxy, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4-Alkyl-S-C1-C4-alkyl, C1-C4-Alkyl-S(O)-C1-C4-alkyl und C1-C4-Alkyl-S(O)2-C1-C4-alkyl steht,
R20
für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, Nitro, Amino, Hydroxy, C1-C6-Alkyl, C1-C6-Halogenalkyl, Cyano-C1-C6-alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, C3-C6-Cycloalkyl (welches gegebenenfalls durch Halogen, Cyano, C1-C4-Alkyl und C3-C6-Cycloalkyl substituiert ist), C3-C6-Cycloalkyl-C1-C6-alkyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C3-C6-Alkenyloxy, C3-C6-Alkinyloxy, C3-C6-Cycloalkyloxy, C1-C6-Alkylcarbonyloxy, C2-C6-Alkenylcarbonyloxy, C2-C6-Alkinylcarbonyloxy, C3-C6-Cycloalkylcarbonyloxy, C1-C6-Alkoxycarbonyloxy, C1-C6-Alkylsulfonyloxy, C1-C6-Alkylamino, C3-C6-Alkenylamino, C3-C6-Alkinylamino, C3-C6-Cycloalkylamino, C1-C6-Alkylthio, C1-C6-Halogenalkylthio, C3-C6-Alkenylthio, C3-C6-Alkinylthio, C3-C6-Cycloalkylthio, C1-C6-Alkylsulfinyl, C1-C6-Alkylsulfonyl, C1-C6-Alkylcarbonyl, C1-C6-Alkoxyimino-C1-C6-alkyl, C1-C6-Alkoxycarbonyl, Aminocarbonyl, C1-C6-Alkylaminocarbonyl, Di-(C1-C6-alkyl)-aminocarbonyl, Aminothiocarbonyl, C1-C6-Alkylaminosulfonyl, C1-C6-Alkylsulfonylamino, C1-C6-Alkylcarbonylamino, C1-C6-Alkylthiocarbonylamino, jeweils gegebenenfalls durch einen Rest aus der Reihe Halogen, Cyano, Nitro, Amino, Hydroxy, C1-C6-Alkyl oder C1-C6-Halogenalkyl substituiertes Phenyl, Phenoxy, Pyridinyl und Pyridinyloxy steht,
R21
für einen Rest aus der Reihe Wasserstoff, C1-C6-Alkyl, C3-C6-Cycloalkyl, C1-C6-Halogenalkyl, C3-C6-Alkenyl, C2-C6-Alkinyl, C3-C6-Cycloalkyl-C1-C6-alkyl, Cyano-C1-C6-alkyl, C1-C6-Alkylcarbonyl, C2-C6-Alkenylcarbonyl, C1-C6-Halogenalkylcarbonyl, C2-C6-Halogenalkenylcarbonyl, C1-C6-Alkoxy-C1-C6-alkyl, C1-C6-Alkoxycarbonyl, C1-C6-Alkylsulfonyl und C1-C6-Halogengenalkylsulfonyl steht,
R23
für einen Rest aus der Reihe Wasserstoff, C1-C6-Alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkenyl, C1-C6-Alkoxy, C2-C6-Alkenyloxy, C2-C6- Alkinyloxy, C3-C6-Cycloalkyloxy, C1-C4-Alkylthio-C1-C4-alkyl, C2-C4-Alkenylthio- C1- C4-alkyl, Cyano-C1-C4-alkyl, C1-C4-Alkoxy-C1-C4-alkyl steht,
oder, für R2 = g),
R22 und R23
gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen gesättigten Ring bilden, der ein oder mehrere weitere Heteroatome aus der Reihe Stickstoff, Sauerstoff und Schwefel enthalten kann, und
R24
für Wasserstoff oder einen jeweils gegebenenfalls durch Halogen oder Cyano substituierten Rest aus der Reihe C1-C4-Alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, Phenyl und Phenyl-C1-C2-alkyl steht,
R25
für Wasserstoff oder einen jeweils gegebenenfalls durch Halogen oder Cyano substituierten Rest aus der Reihe C1-C4-Alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, Phenyl und Phenyl-C1-C2-alkyl steht,
R26
für einen Rest aus der Reihe Wasserstoff, C1-C4-Alkyl, C1-C4-Halogenalkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C4-alkyl, C1-C4-Alkoxy-C1-C2-alkyl, C1-C6-Alkylsulfanyl, C1-C6-Halogenalkylsulfanyl C1-C6-Alkylsulfinyl, C1-C6-Halogenalkylsulfinyl, C1-C6-Alkylsulfonyl, C1-C4-Alkylthio-C1-C2-alkyl, C1-C4-Alkylsulfinyl-C1-C2-alkyl, C1-C4-Alkylsulfonyl-C1-C2-alkyl und Cyano-C1-C4-alkyl steht und
R27
für Wasserstoff, C1-C4-Alkyl, C1-C4-Halogenalkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C4-alkyl, C1-C4-Alkoxy-C1-C2-alkyl, C1-C4-Alkylthio-C1-C2-alkyl, C1-C4-Alkylsulfinyl-C1-C2-alkyl, C1-C4-Alkylsulfonyl-C1-C2-alkyl oder Cyano-C1-C4-alkyl steht.
Preferred range (1): Preference is given to compounds of the formula (I) in which
A
for an A-residue from the series (Ab) and (Af)
Figure imgb0075
 wherein the dashed line represents the bond to the carbon atom of the bicyclic of the formula (I), and
B 2
a radical selected from the group consisting of hydrogen, halogen, C 1 -C 6 -alkyl and C 1 -C 4 -haloalkyl,
Q
stands for sulfur,
R 1
a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl and C 1 -C 6 -alkoxy,
R 2
a) for a B residue from the series
Figure imgb0076
Figure imgb0077
Figure imgb0078
Figure imgb0079
Figure imgb0080
Figure imgb0081
Figure imgb0082
Figure imgb0083
Figure imgb0084
 wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R 2
b) for a D radical from the series (D-1) to (D-3)
Figure imgb0085
 wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R 2
c) a radical of the formula
Figure imgb0086
 wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R 2
d) for a radical of the formula
Figure imgb0087
 wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R 2
e) for an F radical from the series (F-1), (F-8), (F-10) and (F-11)
Figure imgb0088
Figure imgb0089
 wherein the dashed line represents the bond to the carbon atom in the formula (I), or
R 2
f) is a radical from the series C 1 -C 6 -haloalkyl and carboxyl, or
R 2
g) for a radical of the formula
Figure imgb0090
 wherein the dotted line represents the bond to the carbon atom of the bicyclic moiety of formula (I) wherein
G 2
is hydrogen or a radical selected from halogen, nitro, amino, cyano, C 1 -C 4 -alkylamino, halo-C 1 -C 4 -alkylamino, di- (C 1 -C 4 -alkyl) -amino, C 1 -C 4 alkyl, halo-C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkenyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 alkyl, C C 1 -C 4 -alkoxy, halogeno-C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, halogenated C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, Bis (C 1 -C 4 alkoxy) C 1 -C 4 alkyl, bis (halo C 1 -C 4 alkoxy) C 1 -C 4 alkyl, C 1 -C 4 alkoxy (C C 1 -C 4 -alkylsulfanyl) C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy- (C 1 -C 4 -alkylsulfinyl) C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy- (C 1 -C 4 -alkylsulfonyl) C 1 -C 4 - alkyl, bis (C 1 -C 4 alkylsulfanyl) C 1 -C 4 alkyl, bis (haloC 1 -C 4 alkylsulfanyl) C 1 -C 4 alkyl, bis (hydroxyC 1 -C 4- alkylsulfanyl) -C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl, alpha -hydroxyimino-C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 alkyl, alpha -C 1 -C 4 alkoxy-imino-C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 alkyl, C (X 2) NR 3 R 4, NR 6 R 7, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylthio, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, the heterocyclyl Dioxanyl, dioxolanyl, dioxepanyl, dioxocanyl, oxathianyl, oxathiolanyl, oxathiepanyl, oxathiocanyl, dithianyl, dithiolanyl, dithiepanyl, dithiocanyl, oxathianyloxide, oxathiolanyloxide, oxathialpanyloxide, oxathiocanyloxide, oxathianyl dioxide, oxathiolanyl dioxide, oxathiepanyl dioxide, oxathiocanyl dioxide, morpholinyl, Triazolinonyl, oxazolinyl, dihydrooxadiazinyl, dihydrodioxazinyl, dihydrooxazolyl, dihydrooxazinyl and pyrazolinonyl (which in turn may themselves be substituted by C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy and C 1 - C 4 alkoxy-C 1 -C 4 alkyl), phenyl (which in turn may itself be substituted by halogen, cyano, nitro, C 1 -C 4 alkyl and halogeno-C 1 -C 4 alkyl), the heteroaryl radicals Pyridyl, pyridyl- N- oxide, pyrimidyl, imidazolyl, pyrazolyl, oxazolyl, thiazolyl, furanyl, thienyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyrazinyl, triazinyl, tetrazinyl and isoquinolinyl (which in turn may be substituted by halogen, nitro, C C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halogeno-C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl , C 1 -C 4 -alkylthio, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl and C 3 -C 6 -cycloalkyl) and the heteroaryl-C 1 -C 4 -alkyl radicals triazolyl-C 1 -C 4- alkyl, pyridyl-C 1 -C 4 -alkyl, pyrimidyl C 1 -C 4 -alkyl and oxadiazolyl-C 1 -C 4 -alkyl (which in turn may themselves be substituted by halogen and C 1 -C 4 -alkyl),
or
G 2
for a C-residue from the series (C-1) and (C-6) to (C-9)
Figure imgb0091
Figure imgb0092
 wherein the dashed line indicates the bond to the B radicals,
X
stands for oxygen or sulfur,
X 1
a radical selected from the group consisting of hydrogen, halogen, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy and C 1 -C 6 -haloalkoxy stands,
X 2
is oxygen, sulfur, NR 5 or NOH,
VZ
R 24 is CH-CHR 25 or R 24 is C = CR 25 ,
n
stands for 1 or 2,
R
for NR 18 R 19 or for any C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 1 -, optionally substituted by halogen, oxygen (leads to C = O) or cyano, C 6 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -alkyl-SC 1 -C 4 -alkyl, C 1 -C 6 -alkyl-S (O) -C 1 -C 4 -alkyl, C 1 -C 6 -alkyl-S (O) 2 -C 1 -C 4 -alkyl, for R 18 -CO-C 1 -C 4 -alkyl, for NR 18 R 19 -CO-C 1 -C 4 - alkyl, for optionally mono- or disubstituted by oxygen (leads to C = O), C 1 -C 4 -alkyl, C 3 -C 8 -cycloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkyl substituted C C 3 -C 6 -cycloalkyl, optionally optionally mono- or disubstituted by oxygen (leads to C = O), C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkyl-substituted C 3 -C 8 -cycloalkenyl, optionally mono- or disubstituted by oxygen (leads to C = O), C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkyl-substituted C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, for gege appropriate, once or twice by oxygen (leading to C = O), C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy and C 1 -C 4 -halogenoalkyl-substituted C 3 -C 6 -Cycloalkenyl-C 1 -C 4 -alkyl, optionally optionally mono- or disubstituted by oxygen (leads to C = O), C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkyl-substituted heterocyclyl, optionally optionally mono- or disubstituted by oxygen (leads to C = O), C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkyl-substituted heterocyclyl-C 1 -C 4 -alkyl or in each case optionally mono- to trisubstituted by halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -Cycloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy-substituted phenyl, phenyl-C 1 -C 4 -alkyl, hetaryl and hetaryl-C 1 -C 4 -alkyl,
R 3
is hydrogen or C 1 -C 6 -alkyl,
R 4
a radical selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 2 -C 4 -alkynyl, C 3 -C 6 - Cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl- C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, aryl, aryl-C 1 -C 4 -alkyl and hetaryl-C 1 -C 4 -alkyl,
R 5
a radical selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 2 -C 4 -alkynyl, C 3 -C 6 - Cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl- C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, aryl, aryl-C 1 -C 4 -alkyl and hetaryl-C 1 -C 4 -alkyl, or
R 3 and R 4
together with the nitrogen atom to which they are attached form a 4- to 7-membered ring which may contain one or two further nitrogen, oxygen and sulfur heteroatoms (oxygen and sulfur atoms not being immediately adjacent);
R 6
is hydrogen or C 1 -C 4 -alkyl,
R 7
a radical selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 2 -C 4 -alkynyl, C 3 -C 6 - Cycloalkyl, C 3 -C 4 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halogeno-C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 - alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, aryl, aryl-C 1 -C 4- alkyl or hetaryl-C 1 -C 4 alkyl, or
R 6 and R 7
together with the nitrogen atom to which they are attached form a 4- to 7-membered ring which may contain one or two further nitrogen, oxygen and sulfur heteroatoms (oxygen and sulfur atoms not being immediately adjacent);
R 8
a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, cyano-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, in each case optionally halogen-substituted C 1 -C 6 -alkylcarbonyl and C 1 -C 6 -alkylsulfonyl, optionally C-substituted by halogen C 1 -C 6 -alkoxycarbonyl and optionally substituted by halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkyl and cyano-substituted C 3 -C 6 -cycloalkylcarbonyl, or a cation or is an ammonium ion which is optionally substituted by C 1 -C 6 -alkyl or aryl-C 1 -C 6 -alkyl,
R 9
in each case a radical from the series in each case by halogen, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulfinyl , C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl and C 1 -C 6 -haloalkylsulfonyl-substituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl and C 2 -C 6 -alkynyl, respectively optionally substituted by halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy or C 1 -C 6 -haloalkoxy-substituted C 3 -C 6 cycloalkyl, C 3 -C 6 - Cycloalkyl-C 1 -C 6 -alkyl and C 3 -C 6 -cycloalkenyl, in which a ring member by a heteroatom selected from the group sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen may be replaced (and in particular for
Figure imgb0093
 wherein the arrow in each case marks the bond to the S atom in the radical (C-1) and in the radical (F-1)), in each case optionally by halogen, cyano (also in the alkyl part), nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, Amino, C 1 -C 6 -alkylamino, di- (C 1 -C 6 -alkyl) -amino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -alkoxycarbonylamino, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 6- alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl or aminocarbonyl-substituted aryl, heteroaryl, aryl-C 1 -C 6 -alkyl, heteroaryl-C 1 -C 6 -alkyl or NR'R in which R 'and R "independently of one another represent a radical from the series consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy , C 1 -C 6 -alkylcarbonyl and C 1 -C 6 -alkoxylcarbonyl, or
R 8 and R 9
may in the radical (C-1) and in the radical (F-1) together with the NS (O) n group to which they are attached, a saturated or unsaturated and optionally halogen, C 1 -C 6 alkyl , C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy-substituted 5- to 7-membered ring, which form one or two heteroatoms from the series sulfur, oxygen (where oxygen atoms are not immediately may be adjacent) and contain nitrogen and / or at least one and preferably one carbonyl group, in particular R 8 and R 9 may together with the NS (O) n group to which they are attached, stand for a residue from the series
Figure imgb0094
Figure imgb0095
 (in which the arrow in each case marks the bond to the C (X) group),
R 15
in each case a radical from the series in each case optionally substituted by methyl, cyano, carbamoyl, substituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl and C 2 -C 6 -alkynyl, in each case optionally by methyl, trifluoromethyl, halogen, cyano or carbamoyl, substituted C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 2 -alkyl and C 3 -C 6 -cycloalkenyl, in which the rings contain at least one heteroatom from the series sulfur, oxygen ( where oxygen atoms are not immediately adjacent) and may contain nitrogen, each optionally substituted by C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -haloalkylsulfonyl, C 1 -C 4 -alkylamino, di (C 1 -C 4 -alkyl) - amino, halogen, nitro or cyano-substituted aryl, heteroaryl, aryl-C 1 -C 4 -alkyl and heteroaryl-C 1 -C 2 -alkyl and an optionally C 1 -C 4 alkyl, C 1 -C 4 alkylcarbonyl , C 1 -C 4 alkyl C 1 -C 4 -alkoxycarbonyl or C 1 -C 4 -alkylsulfonyl-substituted amino group,
R 8 and R 15
in the radical (C-6) together with the NS (O) n group to which they are attached, can form a saturated or unsaturated and optionally substituted 4- to 8-membered ring containing one or two further heteroatoms from the Sulfur, oxygen (oxygen and sulfur atoms may not be immediately adjacent), and nitrogen and / or at least one carbonyl group,
R 16
a radical from the series hydrogen, in each case optionally substituted by methyl, cyano, carbamoyl or carboxyl-substituted C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 2 -C 4 alkenyl and C 2 -C 4 alkynyl optionally in each case by halogen, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, amino, C 1 -C 6 -alkylamino, di- (C 1 -C 6 -alkyl) -amino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -alkoxycarbonylamino, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C 1 -C 6 alkylcarbonyl-substituted C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl and C 3 -C 6 -cycloalkenyl in which the rings are at least one Heteroatom selected from the group sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen, each g optionally halogen, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, amino, C 1 -C 6 -alkylamino, di (C 1 -C 6 -alkyl) -amino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -alkoxycarbonylamino, C 2 -C 6 -alkenyl, C 2 -C 6 - Alkynyl or C 1 -C 6 alkylcarbonyl-substituted aryl, heteroaryl, aryl-C 1 -C 2 -alkyl and heteroaryl-C 1 -C 2 -alkyl and an optionally C 1 -C 6 -alkyl, C 1 -C 6 Haloalkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkylsulfinyl , C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C 1 -C 6 -alkylcarbonyl-substituted amino group stands,
R 17
in each case a radical from the series in each case by halogen, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulfinyl , C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl or C 1 -C 6 -haloalkylsulfonyl-substituted C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl and C C 2 -C 6 -alkynyl, in each case optionally substituted by halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy or C 1 -C 6 -haloalkoxy-substituted C 3 -C 6 - Cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkenyl, N-pyrrolidinyl, N-piperidinyl, N-morpholinyl, N-thiomorpholinyl, N-thiomorpholinyl-1-oxide, N-thiomorpholinyl-1,1-dioxide, N-piperazinyl, N-1-methylpiperazinyl and N-2-oxo-1-methylpiperazinyl, in each case optionally by halogen, cyano (also in the alkyl part), nitro, C 1 -C 6 - Alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -halogena alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, Amino, C 1 -C 6 -alkylamino, di- (C 1 -C 6 -alkyl) -amino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -alkoxycarbonylamino, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C Aryl, heteroaryl, aryl-C 1 -C 6 -alkyl, heteroaryl-C 1 -C 6 -alkyl and NR'R substituted by 6- alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl or aminocarbonyl in which R 'and R "independently of one another in each case represent a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy C 1 -C 6 -alkylcarbonyl and C 1 -C 6 -alkoxylcarbonyl,
R 8 and R 17
may in the radical (C-8) and in the radical (F-8) together with the NC (X) group to which they are attached, a saturated or unsaturated and optionally halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy form substituted 5- to 7-membered ring which (one or two further heteroatoms from the series comprising sulfur, oxygen, wherein oxygen atoms are not directly adjacent and may contain nitrogen and / or a carbonyl group, in particular R 8 and R 17 may be taken together with the NC (X) group to which they are attached, for a radical from the series
Figure imgb0096
Figure imgb0097
 (in which the arrow in each case marks the bond to the S atom in the radical (C-8) and in the radical (F-8)),
R 18
a radical from the series hydrogen, hydroxy, in each case optionally mono- or polysubstituted by halogen or mono- or di-cyano-substituted C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxy-C 1 -C 4 alkyl, C 1 -C 6 alkyl-SC 1 -C 4 alkyl, C 1 -C 6 alkyl -S (O) -C 1 -C 4 alkyl, C 1 -C 6 alkyl -S (O) 2 -C 1 -C 4 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 3 - C 6 -cycloalkyl-C 1 -C 3 -alkyl, C 3 -C 6 -cycloalkenyl-C 1 -C 3 -alkyl, heterocyclyl, heterocyclyl-C 1 -C 3 -alkyl and in each case optionally just to four times by C 1 - C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 3 -C 6 cycloalkyl, halogen or cyano substituted phenyl, phenylC 1 -C 3 alkyl, hetaryl and hetaryl-C 1 -C 3 -alkyl,
R 19
is hydrogen, an alkali metal or alkaline earth metal ion or an optionally monosubstituted to monosubstituted by C 1 -C 4 -alkyl-substituted ammonium ion or an optionally mono- or polysubstituted by halogen or mono- or disubstituted cyano-substituted radical of the C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkyl-SC 1 -C 4 -alkyl, C C 1 -C 4 -alkyl-S (O) -C 1 -C 4 -alkyl and C 1 -C 4 -alkyl-S (O) 2 -C 1 -C 4 -alkyl,
Y 3
a radical selected from the group consisting of hydrogen, halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 - Haloalkoxy and NR 20 R 21 ,
W
is a radical from the series O, S, SO and SO 2 ,
R 22
a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -haloalkyl, cyano-C 1 -C 6 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, optionally C 1 -C 6 -alkoxy-C 1 -C 6 -substituted by halogen alkyl, optionally halogen-substituted bis (C 1 -C 6 -alkoxy) C 1 -C 6 -alkyl, optionally halogen-substituted C 1 -C 6 -alkylsulfanyl-C 1 -C 6 -alkyl, optionally halogen-substituted C C 1 -C 4 -alkylcarbonyl-C 1 -C 4 -alkyl, optionally halogen-substituted C 1 -C 6 -alkylsulfinyl-C 1 -C 6 -alkyl, optionally C 1 -C 6 -alkylsulfonyl-C 1 substituted by halogen - C 6 alkyl, di- (C 1 -C 6 alkyl) -aminosulfanyl-C 1 -C 6 alkyl, di- (C 1 -C 6 alkyl) -aminosulfinyl-C 1 -C 6 alkyl, di - (C 1 -C 6 -alkyl) -aminosulfonyl-C 1 -C 6 -alkyl, optionally substituted by halogen C 1 -C 6 alkoxycarbonyl, optionally substituted by halogen subs substituted C 1 -C 6 -alkoxycarbonyl-C 1 -C 6 -alkyl, optionally halogen-substituted C 2 -C 4 -alkynyloxy, optionally halogen-substituted C 2 -C 4 -alkoxyloxycarbonyl, di- (C 1 -C 6 - alkyl) -aminocarbonyl, NC 1 -C 6 -alkyl-NC 3 -C 6 -cycloalkylaminocarbonyl, di- (C 1 -C 6 -alkyl) -aminocarbonyl-C 1 -C 6 -alkyl, NC 1 -C 6 -alkyl -NC 3 -C 6 -cycloalkylaminocarbonyl-C 1 -C 6 -alkyl, heterocyclylcarbonyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, optionally substituted by halogen, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl or hetaryl (which may be themselves C 1 -C 6) Substituted alkyl or halogen) substituted C 3 -C 6 -cycloalkyl, optionally substituted by halogen, cyano, nitro, C C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 - C 6 -haloalkoxycarbonyl or hetaryl (which is optionally itself substituted by C 1 -C 6 -alkyl or halogen) substituted C 3 -C 6 -cycloalkylcarbonyl, optionally substituted by halogen, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl or hetaryl (which is optionally itself substituted by C 1 -C 6 -alkyl or halogen) substituted C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, optionally substituted by halogen, cyano (also in the C 1 -C 6 -alkyl portion of heterocyclyl-C C 1 -C 6 -alkyl), nitro, hydroxy, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl (which is optionally substituted by halogen, cyano, C 1 -C 6 -alkyl and C 3 -C 6 cycloalkyl is substituted), C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 -A lkylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 haloalkylsulfonyl, amino, C 1 -C 6 - alkylamino, Di- (C 1 -C 6 -alkyl) amino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -alkoxycarbonylamino, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 - Alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl or aminocarbonyl-substituted heterocyclyl-C 1 -C 6 -alkyl, where appropriate by halogen, cyano, nitro, hydroxyl, amino, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl (which is optionally substituted by halogen, cyano, C 1 -C 6 -alkyl and C 3 -C 6 -cycloalkyl), C 1 -C 6 -alkoxy or C 1 -C 6 -haloalkoxy substituted Aryl, optionally by halogen, cyano (also in the C 1 -C 6 -alkyl portion of aryl-C 1 -C 6 -alkyl), nitro, hydroxy, amino, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl , C 3 -C 6 -cycloalkyl (which is optionally substituted by halogen, cyano, C 1 -C 6 -alkyl and C 3 -C 6 -cycloalkyl), C 1 -C 6 -alkoxy or C 1 -C 6 -haloalkoxy substituted aryl-C C 1 -C 6 -alkyl, where appropriate by halogen, cyano (also in the C 1 -C 6 -alkyl portion of hetaryl-C 1 -C 6 -alkyl), nitro, hydroxy, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl (which is optionally substituted by halogen, cyano, C 1 -C 6 -alkyl and C 3 -C 6 -cycloalkyl), C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 - Haloalkylsulfonyl, amino, C 1 -C 6 -alkylamino, di- (C 1 -C 6 -alkyl) -amino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -alkoxycarbonylamino, C 1 -C 6 -alkoxy C 1 -C 6 -alkyl, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkyl-C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl or aminocarbonyl-substituted hetaryl-C 1 -C 6 -alkyl, or
R 22
for a residue from the series (D-1) to (D-3)
Figure imgb0098
 from the series (E-1) to (E-11)
Figure imgb0099
Figure imgb0100
Figure imgb0101
 and (E-18) to (E-51)
Figure imgb0102
Figure imgb0103
Figure imgb0104
Figure imgb0105
Figure imgb0106
Figure imgb0107
Figure imgb0108
Figure imgb0109
Figure imgb0110
Figure imgb0111
 stands, or
in case R 2 = d),
R 22
also for an E-rest from the series E-12 to E-17
Figure imgb0112
Figure imgb0113
 stands,
R 20
a radical from the group consisting of hydrogen, halogen, cyano, nitro, amino, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, cyano-C 1 -C 6 -alkyl, C 2 -C 6 - Alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl (which is optionally substituted by halogen, cyano, C 1 -C 4 -alkyl and C 3 -C 6 -cycloalkyl), C 3 -C 6 - Cycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 -cycloalkyloxy, C 1 -C 6 -alkylcarbonyloxy, C 2 -C 6 -alkenylcarbonyloxy, C 2 -C 6 -alkynylcarbonyloxy, C 3 -C 6 -cycloalkylcarbonyloxy, C 1 -C 6 -alkoxycarbonyloxy, C 1 -C 6 -alkylsulfonyloxy, C 1 -C 6 -alkylamino, C 3 -C 6 -alkenylamino, C 3 -C 6 -alkynylamino, C 3 -C 6 -cycloalkylamino, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 3 -C 6- alkenylthio, C 3 -C 6 -alkynylthio, C 3 -C 6 -cycloalkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 - Alkoxyimino-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl, Ami carbonyl, C 1 -C 6 alkylaminocarbonyl, di (C 1 -C 6 alkyl) aminocarbonyl, aminothiocarbonyl, C 1 -C 6 alkylaminosulphonyl, C 1 -C 6 alkylsulphonylamino, C 1 -C 6 alkylcarbonylamino, C 1 -C 6 -Alkylthiocarbonylamino, each optionally substituted by a radical selected from halogen, cyano, nitro, amino, hydroxy, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl substituted phenyl, phenoxy, pyridinyl and pyridinyloxy .
R 21
a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, cyano-C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 2 -C 6 -alkenylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 2 -C 6 -haloalkenylcarbonyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylsulfonyl and C 1 -C 6 -halogeno-alkylsulfonyl,
R 23
a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 1 -C 6 alkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy, C 3 -C 6 cycloalkyloxy, C 1 -C 4 alkylthio-C 1 -C 4 alkyl, C 2 -C 4- alkenylthio-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl,
or, for R 2 = c) or g),
R 22 and R 23
together with the nitrogen atom to which they are attached form a saturated ring which may contain one or more further nitrogen, oxygen and sulfur heteroatoms, and
R 24
is hydrogen or a radical optionally substituted by halogen or cyano radical from the series C 1 -C 4 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, phenyl and phenyl-C 1 -C 2 alkyl stands,
R 25
is hydrogen or a radical optionally substituted by halogen or cyano radical from the series C 1 -C 4 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, phenyl and phenyl-C 1 -C 2 alkyl stands,
R 26
a radical selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl C 1 -C 6 Alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 4 -alkylthio-C 1 -C 2 -alkyl, C 1 -C 4 -alkylsulfinyl-C 1 -C 2 -alkyl , C 1 -C 4 -alkylsulfonyl-C 1 -C 2 -alkyl and cyano-C 1 -C 4 -alkyl and
R 27
is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 2 -alkyl, C 1 -C 4 -alkylsulfinyl-C C 1 -C 2 -alkyl, C 1 -C 4 -alkylsulfonyl-C 1 -C 2 -alkyl or cyano-C 1 -C 4 -alkyl and
Compounds of the formula (I) in which
A
for the A-rest
Figure imgb0114
 wherein the dashed line represents the bond to the carbon atom of the bicyclic of the formula (I), and
G 1
stands for N or CB 1 ,
B 1
a radical selected from the group consisting of hydrogen, halogen, C 1 -C 6 -alkyl and C 1 -C 4 -haloalkyl,
B 2
a radical selected from the group consisting of hydrogen, halogen, C 1 -C 6 -alkyl and C 1 -C 4 -haloalkyl,
T
stands for oxygen or a pair of electrons,
Q
stands for sulfur,
R 1
a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl and C 1 -C 6 -alkoxy,
R 2
a) for a B residue from the series
Figure imgb0115
Figure imgb0116
Figure imgb0117
Figure imgb0118
Figure imgb0119
Figure imgb0120
Figure imgb0121
Figure imgb0122
Figure imgb0123
 wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R 2
c) a radical of the formula
Figure imgb0124
 wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R 2
d) for a radical of the formula
Figure imgb0125
 wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R 2
e) for an F radical from the series (F-8), (F-10) and (F-11)
Figure imgb0126
Figure imgb0127
 wherein the dashed line represents the bond to the carbon atom in the formula (I), or
R 2
f) is a radical from the series C 1 -C 6 -haloalkyl and carboxyl, or
R 2
g) for a radical of the formula
Figure imgb0128
 wherein the dotted line represents the bond to the carbon atom of the bicyclic moiety of formula (I) wherein
G 2
is hydrogen or a radical selected from halogen, nitro, amino, cyano, C 1 -C 4 -alkylamino, halo-C 1 -C 4 -alkylamino, di- (C 1 -C 4 -alkyl) -amino, C 1 -C 4 alkyl, halo-C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkenyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 alkyl, C C 1 -C 4 -alkoxy, halogeno-C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, halogenated C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, Bis (C 1 -C 4 alkoxy) C 1 -C 4 alkyl, bis (halo C 1 -C 4 alkoxy) C 1 -C 4 alkyl, C 1 -C 4 alkoxy (C 1 -C 4 alkylsulfanyl) -C 1 -C 4 alkyl, C 1 -C 4 alkoxy (C 1 -C 4 alkylsulfinyl) -C 1 -C 4 alkyl, C 1 -C 4 alkoxy (C 1 -C 4 -alkylsulfonyl) C 1 -C 4 -alkyl, Bis (C 1 -C 4 -alkylsulfanyl) C 1 -C 4 -alkyl, bis (haloC 1 -C 4 -alkylsulfanyl) C 1 -C 4 -alkyl, bis (hydroxy-C 1 -C 4 - alkylsulfanyl) -C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl, alpha -hydroxyimino-C 1 -C 4 -alkoxycarbonyl-C 1 - C 4 alkyl, alpha -C 1 -C 4 alkoxy-imino-C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 alkyl, C (X 2) NR 3 R 4, NR 6 R 7, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylthio, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, the heterocyclyl dioxanyl, dioxolanyl, dioxepanyl, Dioxocanyl, Oxathianyl, Oxathiolanyl, Oxathiepanyl, Oxathiocanyl, dithianyl, dithiolanyl, Dithiepanyl, Dithiocanyl, Oxathianyloxid, Oxathiolanyloxid, Oxathiepanyloxid, Oxathiocanyloxid, Oxathianyldioxid, Oxathiolanyldioxid, Oxathiepanyldioxid, Oxathiocanyldioxid, morpholinyl, Triazolinonyl, oxazolinyl, Dihydrooxadiazinyl, Dihydrodioxazinyl, dihydrooxazolyl, Dihydrooxazinyl and pyrazolinonyl (w which in turn may themselves be substituted by C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl), Phenyl (which in turn may itself be substituted by halogen, cyano, nitro, C 1 -C 4 -alkyl and halogeno-C 1 -C 4 -alkyl), the heteroaryl radicals pyridyl, pyridyl- N- oxide, pyrimidyl, imidazolyl, pyrazolyl, Oxazolyl, thiazolyl, furanyl, thienyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyrazinyl, triazinyl, tetrazinyl and isoquinolinyl (which themselves may be substituted by halo, nitro, C 1 -C 4 alkyl, haloC 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halo-C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio, C 1 -C 4 Alkylthio-C 1 -C 4 -alkyl and C 3 -C 6 -cycloalkyl) and the heteroaryl-C 1 -C 4 -alkyl radicals triazolyl-C 1 -C 4 -alkyl, pyridyl-C 1 -C 4 -alkyl, Pyrimidyl-C 1 -C 4 -alkyl and oxadiazolyl-C 1 -C 4 -alkyl (which in turn may themselves be substituted by halogen and C 1 -C 4 alkyl), or
G 2
for a C-residue from the series (C-1) and (C-6) to (C-9)
Figure imgb0129
Figure imgb0130
 wherein the dashed line indicates the bond to the B radicals,
X
stands for oxygen or sulfur,
X 2
is oxygen, sulfur, NR 5 or NOH,
VZ
R 24 is CH-CHR 25 or R 24 is C = CR 25 ,
n
stands for 1 or 2,
R 3
is hydrogen or C 1 -C 6 -alkyl,
R 4
a radical selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 2 -C 4 -alkynyl, C 3 -C 6 - Cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl- C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, aryl, aryl-C 1 -C 4 -alkyl and hetaryl-C 1 -C 4 -alkyl,
R 5
a radical selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 2 -C 4 -alkynyl, C 3 -C 6 - Cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl- C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, aryl, aryl-C 1 -C 4 -alkyl and hetaryl-C 1 -C 4 -alkyl, or
R 3 and R 4
together with the nitrogen atom to which they are attached form a 4- to 7-membered ring which may contain one or two further nitrogen, oxygen and sulfur heteroatoms (oxygen and sulfur atoms not being immediately adjacent);
R 6
is hydrogen or C 1 -C 4 -alkyl,
R 7
a radical selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 2 -C 4 -alkynyl, C 3 -C 6 - Cycloalkyl, C 3 -C 4 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halogeno-C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 - alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, aryl, aryl-C 1 -C 4- alkyl or hetaryl-C 1 -C 4 alkyl, or
R 6 and R 7
together with the nitrogen atom to which they are attached form a 4- to 7-membered ring which may contain one or two further nitrogen, oxygen and sulfur heteroatoms (oxygen and sulfur atoms not being immediately adjacent);
R 8
a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, cyano-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, in each case optionally halogen-substituted C 1 -C 6 -alkylcarbonyl and C 1 -C 6 -alkylsulfonyl, optionally C-substituted by halogen C 1 -C 6 -alkoxycarbonyl and optionally substituted by halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkyl and cyano-substituted C 3 -C 6 -cycloalkylcarbonyl, or a cation or is an ammonium ion which is optionally substituted by C 1 -C 6 -alkyl or aryl-C 1 -C 6 -alkyl,
R 9
in each case a radical from the series in each case by halogen, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulfinyl , C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl and C 1 -C 6 -haloalkylsulfonyl-substituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl and C 2 -C 6 -alkynyl, each optionally substituted by halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy or C 1 -C 6 Haloalkoxy-substituted C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl and C 3 -C 6 -cycloalkenyl, in which one ring member is represented by a heteroatom selected from the group consisting of sulfur, oxygen (where Oxygen atoms may not be immediately adjacent) and nitrogen may be replaced (and in particular for
Figure imgb0131
 wherein the arrow in each case marks the bond to the S atom in the radical (C-1) and in the radical (F-1)), in each case optionally by halogen, cyano (also in the alkyl part), nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, amino, C 1 -C 6 alkylamino, di (C 1 -C 6 alkyl ) -amino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -alkoxycarbonylamino, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkoxy-C 1 -C 6 - alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl or Aminocarbonyl-substituted aryl, heteroaryl, aryl-C 1 -C 6 -alkyl, heteroaryl-C 1 -C 6 -alkyl or NR'R ", wherein R 'and R" are independently of one another a radical from the series of hydrogen, C C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl and C 1 -C 6 -alkoxylcarbonyl, or
R 8 and R 9
also in the radical (C-1) together with the NS (O) n group to which they are attached, a saturated or unsaturated and optionally halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl , C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy-substituted 5- to 7-membered ring which form one or two heteroatoms from the group consisting of sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen and / or or at least one and preferably a carbonyl group may contain, in particular R 8 and R 9 together with the NS (O) n group to which they are attached, a radical from the series
Figure imgb0132
Figure imgb0133
 (in which the arrow in each case marks the bond to the C (X) group),
R 15
in each case a radical from the series in each case optionally substituted by methyl, cyano, carbamoyl, substituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl and C 2 -C 6 -alkynyl, in each case optionally by methyl, trifluoromethyl, halogen, cyano or carbamoyl, substituted C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 2 -alkyl and C 3 -C 6 -cycloalkenyl, in which the rings contain at least one heteroatom from the series sulfur, oxygen ( where oxygen atoms are not immediately adjacent) and may contain nitrogen, each optionally substituted by C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -haloalkylsulfonyl, C 1 -C 4 -alkylamino, di (C 1 -C 4 -alkyl) - amino, halogen, nitro or cyano-substituted aryl, heteroaryl, aryl-C 1 -C 4 -alkyl and heteroaryl-C 1 -C 2 -alkyl and an optionally C 1 -C 4 alkyl, C 1 -C 4 alkylcarbonyl , C 1 -C 4 alkyl C 1 -C 4 -alkoxycarbonyl or C 1 -C 4 -alkylsulfonyl-substituted amino group,
R 8 and R 15
in the radical (C-6) together with the NS (O) n group to which they are attached, can form a saturated or unsaturated and optionally substituted 4- to 8-membered ring containing one or two further heteroatoms from the Sulfur, oxygen (oxygen and sulfur atoms may not be immediately adjacent), and nitrogen and / or at least one carbonyl group,
R 16
a radical from the series hydrogen, in each case optionally substituted by methyl, cyano, carbamoyl or carboxyl-substituted C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 2 -C 4 alkenyl and C 2 -C 4 alkynyl optionally in each case by halogen, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, amino, C 1 -C 6 -alkylamino, di- (C 1 -C 6 -alkyl) -amino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -alkoxycarbonylamino, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C 1 -C 6 alkylcarbonyl-substituted C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl and C 3 -C 6 -cycloalkenyl in which the rings are at least one Heteroatom selected from the group sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen, each g optionally halogen, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, amino, C 1 -C 6 -alkylamino, di (C 1 -C 6 -alkyl) -amino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -alkoxycarbonylamino, C 2 -C 6 -alkenyl, C 2 -C 6 - Alkynyl or C 1 -C 6 alkylcarbonyl-substituted aryl, heteroaryl, aryl-C 1 -C 2 -alkyl and heteroaryl-C 1 -C 2 -alkyl and an optionally C 1 -C 6 -alkyl, C 1 -C 6 Haloalkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkylsulfinyl , C 1 -C 6 -haloalkylsulfinyl, Stands for C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C 1 -C 6 -alkylcarbonyl-substituted amino group,
R 17
in each case a radical from the series in each case by halogen, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulfinyl , C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl or C 1 -C 6 -haloalkylsulfonyl-substituted C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl and C C 2 -C 6 -alkynyl, in each case optionally substituted by halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy or C 1 -C 6 -haloalkoxy-substituted C 3 -C 6 - Cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkenyl, N-pyrrolidinyl, N-piperidinyl, N-morpholinyl, N-thiomorpholinyl, N-thiomorpholinyl-1-oxide, N-thiomorpholinyl-1,1-dioxide, N-piperazinyl, N-1-methylpiperazinyl and N-2-oxo-1-methylpiperazinyl, in each case optionally by halogen, cyano (also in the alkyl part), nitro, C 1 -C 6 - Alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -halogena alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, amino, C 1 -C 6 -alkylamino, di- (C 1 - C 6 alkyl) -amino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -alkoxycarbonylamino, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl or aminocarbonyl-substituted aryl, heteroaryl, aryl-C 1 -C 6 -alkyl, heteroaryl-C 1 -C 6 -alkyl and NR'R ", wherein R 'and R" are each independently a radical from the A series of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl and C 1 -C 6 -alkoxylcarbonyl stand,
R 8 and R 17
may in the radical (C-8) and in the radical (F-8) together with the NC (X) group to which they are attached, a saturated or unsaturated and optionally halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy form substituted 5- to 7-membered ring which (one or two further heteroatoms from the series comprising sulfur, oxygen, wherein oxygen atoms are not directly adjacent and may contain nitrogen and / or a carbonyl group, in particular R 8 and R 17 may be taken together with the NC (X) group to which they are attached, for a radical from the series
Figure imgb0134
Figure imgb0135
 (in which the arrow in each case marks the bond to the S atom in the radical (C-8) and in the radical (F-8)),
and in the case where R 2 is g),
R 22
a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -haloalkyl, cyano-C 1 -C 6 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, optionally C 1 -C 6 -alkoxy-C 1 -C 6 -substituted by halogen alkyl, optionally halogen-substituted bis (C 1 -C 6 -alkoxy) C 1 -C 6 -alkyl, optionally halogen-substituted C 1 -C 6 -alkylsulfanyl-C 1 -C 6 -alkyl, optionally halogen-substituted C C 1 -C 4 -alkylcarbonyl-C 1 -C 4 -alkyl, optionally halogen-substituted C 1 -C 6 -alkylsulfinyl-C 1 -C 6 -alkyl, optionally C 1 -C 6 -alkylsulfonyl-C 1 substituted by halogen - C 6 alkyl, di- (C 1 -C 6 alkyl) -aminosulfanyl-C 1 -C 6 alkyl, di- (C 1 -C 6 alkyl) -aminosulfinyl-C 1 -C 6 alkyl, di - (C 1 -C 6 -alkyl) -aminosulfonyl-C 1 -C 6 -alkyl, optionally substituted by halogen C 1 -C 6 -alkoxycarbonyl-C 1 -C 6 -alkyl, optionally du halogen-substituted C 2 -C 4 -alkynyloxy, di- (C 1 -C 6 -alkyl) -aminocarbonyl-C 1 -C 6 -alkyl, NC 1 -C 6 -alkyl-NC 3 -C 6 -cycloalkylaminocarbonyl-C C 1 -C 6 alkyl, heterocyclylcarbonyl C 1 -C 6 alkyl, C 1 -C 6 alkylsulfanyl, C 1 -C 6 haloalkylsulfanyl, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, where appropriate by halogen, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 - C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 haloalkoxycarbonyl or hetaryl (which is optionally itself substituted by C 1 -C 6 alkyl or halogen) substituted C 3 C 6 -C 6 cycloalkyl, optionally substituted by halogen, cyano, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 haloalkoxycarbonyl or hetaryl (which may be itself by C 1 -C 6 alkyl or Halogen substituted) substituted C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, optionally substituted by halogen, cyano (also in the C 1 -C 6 -alkyl portion of heterocyclyl-C 1 -C 6 -alkyl), nitro, Hydroxy, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl (which is optionally substituted by halogen, cyano, C 1 -C 6 -alkyl and C 3 -C 6 -cycloalkyl ), C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -haloalkylsulfonyl, amino, C 1 -C 6 -alkylamino, di- (C 1 -C 6 -alkyl) -amino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 alkoxycarbonylamino, C 1 -C 6 alkoxy-C 1 -C 6 alkyl, C 1 -C 6 haloalkoxy-C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl or aminocarbonyl-substituted heterocyclyl-C 1 -C 6 -alkyl, optionally substituted by Halogen, cyano, nitro, hydr oxy, amino, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl (which is optionally substituted by halogen, cyano, C 1 -C 6 -alkyl and C 3 -C 6 -cycloalkyl substituted), C 1 -C 6 -alkoxy or C 1 -C 6 -haloalkoxy-substituted aryl, optionally substituted by halogen, cyano (also in the C 1 -C 6 -alkyl portion of aryl-C 1 -C 6 -alkyl), nitro , Hydroxy, amino, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl (which is optionally substituted by halogen, Cyano, C 1 -C 6 -alkyl and C 3 -C 6 -cycloalkyl), C 1 -C 6 -alkoxy or C 1 -C 6 -haloalkoxy-substituted aryl-C 1 -C 6 -alkyl, optionally substituted by halogen , Cyano (also in the C 1 -C 6 -alkyl portion of hetaryl-C 1 -C 6 -alkyl), nitro, hydroxy, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 - Cycloalkyl (which is optionally substituted by halogen, cyano, C 1 -C 6 -alkyl and C 3 -C 6 -cycloalkyl), C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 - alkylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 haloalkylsulfonyl, amino, C 1 -C 6 - Alkylamino, di- (C 1 -C 6 -alkyl) amino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -alkoxycarbonylamino, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkyl-C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl or Ami nocarbonyl-substituted hetaryl-C 1 -C 6 -alkyl, and in the case where R 2 is c), d) or g),
R 22
for a residue from the series (D-1) to (D-3)
Figure imgb0136
 wherein
X 1
a radical selected from the group consisting of hydrogen, halogen, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy and C 1 -C 6 -haloalkoxy stands,
R
for NR 18 R 19 or for any C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 1 -, optionally substituted by halogen, oxygen (leads to C = O) or cyano, C 6 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -alkyl-SC 1 -C 4 -alkyl, C 1 -C 6 -alkyl-S (O) -C 1 -C 4 -alkyl, C 1 -C 6 -alkyl-S (O) 2 -C 1 -C 4 -alkyl, for R 18 -CO-C 1 -C 4 -alkyl, for NR 18 R 19 -CO-C 1 -C 4 - alkyl, for optionally mono- or disubstituted by oxygen (leads to C = O), C 1 -C 4 -alkyl, C 3 -C 8 -cycloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkyl substituted C C 3 -C 6 -cycloalkyl, optionally optionally mono- or disubstituted by oxygen (leads to C = O), C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkyl-substituted C 3 -C 8 -cycloalkenyl, optionally mono- or disubstituted by oxygen (leads to C = O), C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkyl-substituted C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, for gege appropriate, once or twice by oxygen (leading to C = O), C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy and C 1 -C 4 -halogenoalkyl-substituted C 3 -C 6 -Cycloalkenyl-C 1 -C 4 -alkyl, optionally optionally mono- or disubstituted by oxygen (leads to C = O), C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkyl-substituted heterocyclyl, optionally optionally mono- or disubstituted by oxygen (leads to C = O), C 1 -C 4 -alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy and C 1 -C 4 -halogenoalkyl-substituted heterocyclyl-Ci-C4-alkyl or represents in each case optionally mono- to trisubstituted by halogen, cyano, C 1 -C 4 - Alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy-substituted phenyl, phenyl-C 1 -C 4 -alkyl, hetaryl and hetaryl- C 1 -C 4 -alkyl,
Y 3
a radical selected from the group consisting of hydrogen, halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 - Haloalkoxy and NR 20 R 21 ,
W
is a radical from the series O, S, SO and SO 2 ,
R 22
furthermore, a radical from the series (E-1) to (E-11)
Figure imgb0137
Figure imgb0138
Figure imgb0139
 and (E-18) to (E-51)
Figure imgb0140
Figure imgb0141
Figure imgb0142
Figure imgb0143
Figure imgb0144
Figure imgb0145
Figure imgb0146
Figure imgb0147
Figure imgb0148
Figure imgb0149
 stands, or
in case R 2 = d),
R 22
also for an E-rest from the series E-12 to E-17
Figure imgb0150
Figure imgb0151
 stands,
R 18
a radical from the series hydrogen, hydroxy, in each case optionally mono- or polysubstituted by halogen or mono- or di-cyano-substituted C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxy-C 1 -C 4 alkyl, C 1 -C 6 alkyl-SC 1 -C 4 alkyl, C 1 -C 6 alkyl -S (O) -C 1 -C 4 alkyl, C 1 -C 6 alkyl -S (O) 2 -C 1 -C 4 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 3 - C 6 -cycloalkyl-C 1 -C 3 -alkyl, C 3 -C 6 -cycloalkenyl-C 1 -C 3 -alkyl, heterocyclyl, heterocyclyl-C 1 -C 3 -alkyl and in each case optionally just to four times by C 1 - C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 3 -C 6 cycloalkyl, halogen or cyano substituted phenyl, phenylC 1 -C 3 alkyl, hetaryl and hetaryl-C 1 -C 3 -alkyl,
R 19
is hydrogen, an alkali or alkaline earth metal ion, or an optionally monosubstituted to monosubstituted by C 1 -C 4 alkyl substituted ammonium ion or each optionally mono- or polysubstituted by halogen or mono- or cyano-substituted radical from the series C 1 -C 4- alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkyl-SC 1 -C 4 -alkyl, C 1 -C 4 - Alkyl-S (O) -C 1 -C 4 -alkyl and C 1 -C 4 -alkyl-S (O) 2 -C 1 -C 4 -alkyl,
R 20
a radical from the group consisting of hydrogen, halogen, cyano, nitro, amino, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, cyano-C 1 -C 6 -alkyl, C 2 -C 6 - Alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl (which is optionally substituted by halogen, cyano, C 1 -C 4 -alkyl and C 3 -C 6 -cycloalkyl), C 3 -C 6 - Cycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 -cycloalkyloxy, C 1 -C 6 -alkylcarbonyloxy, C 2 -C 6 -alkenylcarbonyloxy, C 2 -C 6 -alkynylcarbonyloxy, C 3 -C 6 -cycloalkylcarbonyloxy, C 1 -C 6 -alkoxycarbonyloxy, C 1 -C 6 -alkylsulfonyloxy, C 1 -C 6 -alkylamino, C 3 -C 6 -alkenylamino, C 3 -C 6 -alkynylamino, C 3 -C 6 -cycloalkylamino, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 3 -C 6- alkenylthio, C 3 -C 6 -alkynylthio, C 3 -C 6 -cycloalkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 - Alkoxyimino-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl, Ami carbonyl, C 1 -C 6 alkylaminocarbonyl, di (C 1 -C 6 alkyl) aminocarbonyl, aminothiocarbonyl, C 1 -C 6 alkylaminosulphonyl, C 1 -C 6 alkylsulphonylamino, C 1 -C 6 alkylcarbonylamino, C 1 -C 6 -Alkylthiocarbonylamino, each optionally substituted by a radical selected from halogen, cyano, nitro, amino, hydroxy, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl substituted phenyl, phenoxy, pyridinyl and pyridinyloxy .
R 21
a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, cyano-C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 2 -C 6 -alkenylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 2 -C 6 -haloalkenylcarbonyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylsulfonyl and C 1 -C 6 -halogeno-alkylsulfonyl,
R 23
a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 1 -C 6 alkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy, C 3 -C 6 cycloalkyloxy, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, C 2 -C 4 -alkenylthio-C 1 - C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy C 1 -C 4 -alkyl,
or, for R 2 = g),
R 22 and R 23
together with the nitrogen atom to which they are attached form a saturated ring which may contain one or more further nitrogen, oxygen and sulfur heteroatoms, and
R 24
is hydrogen or a radical optionally substituted by halogen or cyano radical from the series C 1 -C 4 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, phenyl and phenyl-C 1 -C 2 alkyl stands,
R 25
is hydrogen or a radical optionally substituted by halogen or cyano radical from the series C 1 -C 4 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, phenyl and phenyl-C 1 -C 2 alkyl stands,
R 26
a radical selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl C 1 -C 6 Alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 4 -alkylthio-C 1 -C 2 -alkyl, C 1 -C 4 -alkylsulfinyl-C 1 -C 2 -alkyl , C 1 -C 4 -alkylsulfonyl-C 1 -C 2 -alkyl and cyano-C 1 -C 4 -alkyl and
R 27
is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 2 -alkyl, C 1 -C 4 -alkylsulfinyl-C C 1 -C 2 -alkyl, C 1 -C 4 -alkylsulfonyl-C 1 -C 2 -alkyl or cyano-C 1 -C 4 -alkyl.

Vorzugsbereich (2): Besonders bevorzugt sind Verbindungen der Formel (I), worin

A
für einen A-Rest aus der Reihe (A-b) und (A-f)
Figure imgb0152
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet,
B2
für einen Rest aus der Reihe Wasserstoff, Halogen, C1-C6-Alkyl und C1-C4-Halogenalkyl steht,
Q
für Schwefel steht,
R1
für einen Rest aus der Reihe Wasserstoff, C1-C4-Alkyl und C1-C4-Alkoxy steht,
R2
a) für einen B-Rest aus der Reihe
Figure imgb0153
Figure imgb0154
Figure imgb0155
Figure imgb0156
Figure imgb0157
Figure imgb0158
Figure imgb0159
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder
R2
b) für einen D-Rest aus der Reihe (D-1) bis (D-3)
Figure imgb0160
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder
R2
c) für einen Rest der Formel
Figure imgb0161
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder
R2
d) für einen Rest der Formel
Figure imgb0162
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder
R2
e) für einen F-Rest aus der Reihe (F-1), (F-8) und (F-10)
Figure imgb0163
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom in der Formel (I) bedeutet, oder
R2
f) für einen Rest aus der Reihe C1-C6-Halogenalkyl und Carboxyl steht,
R2
g) für einen Rest der Formel
Figure imgb0164
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, worin
G2
für Wasserstoff oder einen Rest aus der Reihe Halogen, Nitro, Amino, Cyano, C1-C4-Alkylamino, Halogen-C1-C4-Alkylamino, Di-(C1-C4-alkyl)-amino, C1-C4-Alkyl, Halogen-C1-C4-alkyl, C1-C4-Alkoxy, Halogen-C1-C4-alkoxy, C1-C4-Alkoxy-C1-C4-alkyl, halogeniertes C1-C4-Alkoxy-C1-C4-alkyl, Bis(C1-C4-alkoxy)-C1-C4-alkyl, Bis(halogen-C1-C4-alkoxy)-C1-C4-alkyl, C1-C4-Alkoxy-(C1-C4-alkylsulfanyl)-C1-C4-alkyl, C1-C4-Alkoxy-(C1-C4-alkylsulfinyl)-C1-C4-alkyl, C1-C4-Alkoxy-(C1-C4-alkylsulfonyl)-C1-C4-alkyl, Bis(C1-C4-alkylsulfanyl)-C1-C4-alkyl, Bis(halogen-C1-C4-alkylsulfanyl)-C1-C4-alkyl, Bis(hydroxy-C1-C4-alkylsulfanyl)-C1-C4-alkyl, C1-C4-Alkoxycarbonyl, C1-C4-Alkoxycarbonyl-C1-C4-alkyl, C(X2)NR3R4, NR6R7, C1-C4-Alkylthio, C1-C4-Alkylsulfinyl, C1-C4-Alkylsulfonyl, C1-C4-Halogenalkylthio, C1-C4-Halogenalkylsulfinyl, C1-C4-Halogenakylsulfonyl, die Heterocyclylreste Dioxanyl, Dioxolanyl, Dioxepanyl, Dioxocanyl, Oxathianyl, Oxathiolanyl, Oxathiepanyl, Oxathiocanyl, Dithianyl, Dithiolanyl, Dithiepanyl, Dithiocanyl, Oxathianyloxid, Oxathiolanyloxid, Oxathiepanyloxid, Oxathiocanyloxid, Oxathianyldioxid, Oxathiolanyldioxid, Oxathiepanyldioxid, Oxathiocanyldioxid, Morpholinyl, Triazolinonyl, Oxazolinyl, Dihydrooxadiazinyl, Dihydrodioxazinyl, Dihydrooxazolyl, Dihydrooxazinyl und Pyrazolinonyl (welche selbst wiederum substituiert sein können durch C1-C4-Alkyl, Halogen-C1-C4-alkyl, C1-C4-Alkoxy und C1-C4-Alkoxy-C1-C4-alkyl), Phenyl (welches selbst wiederum substituiert sein kann durch Halogen, Cyano, Nitro, C1-C4-Alkyl und Halogen-C1-C4-alkyl), die Heteroarylreste Pyridyl, Pyridyl-N-oxid, Pyrimidyl, Imidazolyl, Pyrazolyl, Oxazolyl, Thiazolyl, Furanyl, Thienyl, Triazolyl, Tetrazolyl, Oxadiazolyl, Thiadiazolyl, Pyrazinyl, Triazinyl, Tetrazinyl und Isochinolinyl (welche selbst wiederum substituiert sein können durch Halogen, Nitro, C1-C4-Alkyl, Halogen-C1-C4-alkyl, C1-C4-Alkoxy, Halogen-C1-C4-alkoxy, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4-Alkylthio, C1-C4-Alkylthio-C1-C4-alkyl und C3-C6-Cycloalkyl) und die Heteroaryl-C1-C4-alkylreste Triazolyl-C1-C4-alkyl, Pyridyl-C1-C4-alkyl, Pyrimidyl-C1-C4-alkyl und Oxadiazolyl-C1-C4-alkyl (welche selbst wiederum substituiert sein können durch Halogen und C1-C4-Alkyl), oder
G2
für einen C-Rest aus der Reihe (C-1), (C-6) und (C-9)
Figure imgb0165
 steht, worin die gestrichelte Linie die Bindung zu den B-Resten bedeutet,
X
für Sauerstoff steht,
X1
für einen Rest aus der Reihe Wasserstoff, Fluor, Chlor, Brom, Jod, Cyano, Nitro, C1-C4-Alkyl, C1-C4-Halogenalkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy und C1-C4-Halogenalkoxy steht,
X2
für Sauerstoff, Schwefel, NR5 oder NOH steht,
n
für 2 steht,
R
für NR18R19 oder für jeweils gegebenfalls einfach bis siebenfach durch Halogen, einfach oder zweifach durch Sauerstoff (führt zu C=O) oder einfach oder zweifach durch Cyano substituiertes C1-C6-Alkyl, C3-C6-Alkenyl, C3-C6-Alkinyl, C1-C4-Alkoxy-C1-C3-alkyl, C1-C4-Alkyl-S-C1-C3-alkyl, C1-C4-Alkyl-S(O)-C1-C3-alkyl, C1-C4-Alkyl-S(O)2-C1-C3-alkyl, für R18-CO-C1-C2-alkyl, für NR18R19-CO-C1-C2-alkyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=O), C1-C4-Alkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy und C1-C4-Halogenalkyl substituiertes C3-C6-Cycloalkyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=O), C1-C4-Alkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy und C1-C4-Halogenalkyl substituiertes C3-C8-Cycloalkenyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=O), C1-C4-Alkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy und C1-C4-Halogenalkyl substituiertes C3-C6-Cycloalkyl-C1-C4-alkyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=O), C1-C4-Alkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy und C1-C4-Halogenalkyl substituiertes C3-C6-Cycloalkenyl-C1-C4-alkyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=O), C1-C4-Alkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy und C1-C4-Halogenalkyl substituiertes Heterocyclyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=O), C1-C4-Alkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy und C1-C4-Halogenalkyl substituiertes Heterocyclyl-Ci-C4-alkyl oder für jeweils gegebenenfalls einfach bis dreifach durch Halogen, Cyano, C1-C4-Alkyl, C1-C4-Halogenalkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy oder C1-C4-Halogenalkoxy substituiertes Phenyl, Phenyl-C1-C4-alkyl, Hetaryl und Hetaryl-C1-C4-alkyl steht,
R3
für C1-C4-Alkyl steht,
R4
für einen Rest aus der Reihe Wasserstoff, C1-C4-Alkyl, Halogen-C1-C4-alkyl, Cyano-C1-C4-alkyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C4-alkyl, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4-Alkoxycarbonyl, C1-C4-Alkoxycarbonyl-C1-C4-alkyl und C1-C4-Alkylthio-C1-C4-alkyl steht,
R5
für einen Rest aus der Reihe Wasserstoff, C1-C4-Alkyl, Halogen-C1-C4-alkyl, Cyano-C1-C4-alkyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C4-alkyl, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4-Alkoxycarbonyl, C1-C4-Alkoxycarbonyl-C1-C4-alkyl und C1-C4-Alkylthio-C1-C4-alkyl steht,
R6
für Wasserstoff oder C1-C4-Alkyl steht,
R7
für einen Rest aus der Reihe Wasserstoff, C1-C4-Alkyl, Halogen-C1-C4-alkyl, Cyano-C1-C4-alkyl, C2-C4-Alkinyl, C1-C4-Alkoxy, Halogen-C1-C4-alkoxy, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4-Alkoxycarbonyl, C1-C4-Alkoxycarbonyl-C1-C4-alkyl, C1-C4-Alkylthio-C1-C4-alkyl, Aryl-C1-C4-alkyl oder Hetaryl-C1-C4-alkyl steht, oder
R6 und R7
gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen 4- bis 7-gliedrigen Ring bilden, der ein oder zwei weitere Heteroatome aus der Reihe Stickstoff, Sauerstoff und Schwefel (wobei Sauerstoff- und Schwefelatome nicht unmittelbar benachbart sein dürfen) enthalten kann,
R8
für einen Rest aus der Reihe Wasserstoff, C1-C6-Alkyl, C1-C6-Halogenalkyl, Cyano-C1-C6-alkyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C2-C6-Alkenyl, C1-C6-Alkoxy-C1-C6-alkyl, jeweils gegebenenfalls durch Halogen substituiertes C1-C6-Alkylcarbonyl und C1-C6-Alkylsulfonyl, gegebenenfalls durch Halogen substituiertes C1-C6-Alkoxycarbonyl und gegebenenfalls durch Halogen, C1-C6-Alkyl, C1-C6-Alkoxy, C1-C6-Halogenalkyl und Cyano substituiertes C3-C6-Cycloalkylcarbonyl steht, oder für ein Kation oder ein gegebenenfalls durch C1-C6-Alkyl oder Aryl-C1-C6-alkyl substituiertes Ammonium-Ion steht,
R9
für einen Rest aus der Reihe jeweils gegebenenfalls durch Halogen, C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C1-C4-Alkylthio, C1-C4-Halogenalkylthio, C1-C4-Alkylsulfinyl, C1-C4-Halogenalkylsulfinyl, C1-C4-Alkylsulfonyl und C1-C4-Halogenalkylsulfonyl substituiertes C1-C4-Alkyl, C2-C4-Alkenyl und C2-C4-Alkinyl, jeweils gegebenenfalls durch Halogen, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy substituiertes C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C4-alkyl und C3-C4-Cycloalkenyl, in welchen ein oder zwei Ringglieder jeweils durch ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff ersetzt sein können (und dabei insbesondere für
Figure imgb0166
 wobei der Pfeil jeweils die Bindung zum S-Atom in dem Rest (C-1) und im Rest (F-1) markiert), jeweils gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, C1-C4-Alkyl, C1-C4-Halogenalkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C1-C4-Alkylthio, C1-C4-Halogenalkylthio, C1-C4-Alkylsulfinyl, C1-C4-Halogenalkylsulfinyl, C1-C4-Alkylsulfonyl, C1-C4-Halogenalkylsulfonyl, Amino, C1-C4-Alkylamino, Di-(C1-C4-alkyl)-amino, C1-C4-Alkylcarbonylamino, C1-C4-Alkoxycarbonylamino, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4-Halogenalkoxy-C1-C4-alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl-C1-C4-alkyl, C1-C4-Alkylcarbonyl, C1-C4-Alkoxycarbonyl oder Aminocarbonyl substituiertes Aryl, Heteroaryl, Aryl-C1-C4-alkyl und Heteroaryl-C1-C4-alkyl oder für NR'R" steht, worin R' und R" unabhängig voneinander für einen Rest aus der Reihe Wasserstoff und C1-C4-Alkyl stehen, oder
R8 und R9
können im Rest (C-1) und im Rest (F-1) auch zusammen mit der N-S(O)n Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls durch Halogen, C1-C6-Alkyl, C1-C6-Halogenalkyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy substituierten 5- bis 7-gliedrigen Ring bilden, der ein oder zwei Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine und bevorzugt genau eine Carbonylgruppe enthalten kann, insbesondere können R8 und R9 zusammen mit der N-S(O)n Gruppe, an die sie gebunden sind, für einen Rest aus der Reihe
Figure imgb0167
Figure imgb0168
 stehen (worin der Pfeil jeweils die Bindung zur C(X)-Gruppe markiert),
R15
für einen Rest aus der Reihe jeweils gegebenenfalls durch Methyl substituiertes C1-C6-Alkyl, C2-C6-Alkenyl und C2-C6-Alkinyl und jeweils gegebenenfalls durch Methyl, Halogen, Cyano oder Carbamoyl substituiertes C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C2-alkyl und C3-C6-Cycloalkenyl steht,
R8 und R15
im Rest (C-6) auch zusammen mit der N-S(O)n-Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring bilden können, der ein oder zwei weitere Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoff- und Schwefelatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann,
R17
für einen Rest aus der Reihe jeweils gegebenenfalls durch Halogen, C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C1-C4-Alkylthio, C1-C4-Halogenalkylthio, C1-C4-Alkylsulfinyl, C1-C4-Halogenalkylsulfinyl, C1-C4-Alkylsulfonyl und C1-C4-Halogenalkylsulfonyl substituiertes C1-C4-Alkyl, C2-C4-Alkenyl und C2-C4-Alkinyl, jeweils gegebenenfalls durch Halogen, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy substituiertes C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C4-alkyl, C3-C4-Cycloalkenyl, N-Pyrrolidinyl, N-Piperidinyl, N-Morpholinyl, N-Thiomorpholinyl, N-Thiomorpholinyl-1-oxid, N-Thiomorpholinyl-1,1-dioxid, N-Piperazinyl, N-1-Methylpiperazinyl und N-2-Oxo-1-methylpiperazinyl, jeweils gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, C1-C4-Alkyl, C1-C4-Halogenalkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C1-C4-Alkylthio, C1-C4-Halogenalkylthio, C1-C4-Alkylsulfinyl, C1-C4-Halogenalkylsulfinyl, C1-C4-Alkylsulfonyl, C1-C4-Halogenalkylsulfonyl, Amino, C1-C4-Alkylamino, Di-(C1-C4-alkyl)-amino, C1-C4-Alkylcarbonylamino, C1-C4-Alkoxycarbonylamino, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4-Halogenalkoxy-C1-C4-alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl-C1-C4-alkyl, C1-C4-Alkylcarbonyl, C1-C4-Alkoxycarbonyl oder Aminocarbonyl substituiertes Aryl, Heteroaryl, Aryl-C1-C4-alkyl und Heteroaryl-C1-C4-alkyl oder für NR'R"steht, worin R' und R" unabhängig voneinander für einen Rest aus der Reihe Wasserstoff und C1-C4-Alkyl stehen,
R18
für einen Rest aus der Reihe Wasserstoff, Hydroxy, jeweils gegebenenfalls einfach oder mehrfach durch Halogen oder einfach oder zweifach durch Cyano substituiertes C1-C4-Alkyl, C1-C4-Alkoxy, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4-Alkyl-S-C1-C3-alkyl, C1-C4-Alkyl-S(O)-C1-C3-alkyl, C1-C4-Alkyl-S(O)2-C1-C3-alkyl, C1-C4-Alkylcarbonyl, C1-C4-Alkoxycarbonyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C3-alkyl, Heterocyclyl, Heterocyclyl-C1-C3-alkyl und jeweils gegebenenfalls einfach bis dreifach durch C1-C4-Alkyl, C1-C3-Halogenalkyl, C1-C3-Alkoxy, C1-C3-Halogenalkoxy, Cyclopropyl, Fluor Chlor, Brom oder Cyano substituiertes Phenyl, Benzyl, Pyridyl, Pyrimidyl, Thiazolyl, Oxazolyl, Pyrazolyl, Thienyl, Furanyl, Pyridinylmethyl und Thiazolylmethyl steht,
R19
für Wasserstoff, für ein Alkali- oder Erdalkalimetallion, für ein gegebenfalls einfach bis vierfach durch C1-C4-Alkyl substituiertes Ammoniumion oder für einen jeweils gegebenenfalls einfach oder mehrfach durch Halogen oder einfach oder zweifach durch Cyano substituierten Rest aus der Reihe C1-C4-Alkyl, C1-C4-Alkoxy, C1-C4-Alkoxy-C1-C2-alkyl, C1-C4-Alkyl-S-C1-C2-alkyl, C1-C4-Alkyl-S(O)-C1-C2-alkyl und C1-C4-Alkyl-S(O)2-C1-C2-alkyl steht,
Y3
für einen Rest aus der Reihe Wasserstoff, Fluor, Chlor, Brom, Jod, Cyano, C1-C4-Alkyl, C1-C4-Halogenalkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy und C1-C4-Halogenalkoxy steht,
W
für einen Rest aus der Reihe S, SO und SO2 steht,
R22
für einen Rest aus der Reihe Wasserstoff, C1-C4-Alkyl, C2-C4-Halogenalkyl, Cyano-C1-C4-alkyl, C2-C4-Alkenyl, C2-C4-Halogenalkenyl, C2-C4-Alkinyl, C2-C4-Halogenalkinyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy, gegebenenfalls durch Halogen substituiertes C1-C2-Alkoxy-C1-C4-alkyl, gegebenenfalls durch Halogen substituiertes Bis(C1-C2-alkoxy)-C1-C4-alkyl, gegebenenfalls durch Halogen substituiertes C1-C4-Alkylsulfanyl-C1-C4-alkyl, gegebenenfalls durch Halogen substituiertes C1-C4-Alkylcarbonyl-C1-C4-alkyl, gegebenenfalls durch Halogen substituiertes C1-C4-Alkylsulfinyl-C1-C4-alkyl, gegebenenfalls durch Halogen substituiertes C1-C4-Alkylsulfonyl-C1-C4-alkyl, Di-(C1-C4-alkyl)-aminosulfanyl-C1-C4-alkyl, Di-(C1-C4-alkyl)-aminosulfinyl-C1-C4-alkyl, Di-(C1-C4-alkyl)-aminosulfonyl-C1-C4-alkyl, gegebenenfalls durch Halogen substituiertes C1-C4-Alkoxycarbonyl, gegebenenfalls durch Halogen substituiertes C1-C4-Alkoxycarbonyl-C1-C4-alkyl, gegebenenfalls durch Halogen substituiertes C2-C4-Alkinyloxy, gegebenenfalls durch Halogen substituiertes C2-C4-Alkinyloxycarbonyl, Di-(C1-C4-alkyl)-aminocarbonyl, N-C1-C4-Alkyl-N-C3-C6-cycloalkylaminocarbonyl, Di-(C1-C4-alkyl)-aminocarbonyl-C1-C4-alkyl, N-C1-C4-Alkyl-N-C3-C6-cycloalkylaminocarbonyl-C1-C4-alkyl, Heterocyclylcarbonyl-C1-C4-alkyl, C1-C4-Alkylsulfanyl, C1-C4-Halogenalkylsulfanyl, C1-C4-Alkylsulfinyl, C1-C4-Halogenalkylsulfinyl, C1-C4-Alkylsulfonyl, C1-C4-Halogenalkylsulfonyl, gegebenenfalls durch Halogen, Cyano, Nitro, C1-C4-Alkyl, C1-C4-Halogenalkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C1-C4-Alkoxycarbonyl, C1-C4-Halogenalkoxycarbonyl oder Pyridyl (welches gegebenenfalls selbst durch C1-C4-Alkyl oder Halogen substituiert ist) substituiertes C3-C6-Cycloalkyl, gegebenenfalls durch Halogen, Cyano, Nitro, C1-C4-Alkyl, C1-C4-Halogenalkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C1-C4-Alkoxycarbonyl, C1-C4-Halogenalkoxycarbonyl oder Pyridyl (welches gegebenenfalls selbst durch C1-C4-Alkyl oder Halogen substituiert ist) substituiertes C3-C6-Cycloalkylcarbonyl, gegebenenfalls durch Halogen, Cyano, Nitro, C1-C4-Alkyl, C1-C4-Halogenalkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C1-C4-Alkoxycarbonyl, C1-C4-Halogenalkoxycarbonyl, Pyridyl, Pyrimidyl, Pyrazanyl, Pyridazinyl, Thiazolyl, Isothiazolyl, Thiadiazolyl, Oxazolyl, Isoxazolyl, Oxadiazolyl, Pyrazolyl, Triazinyl oder Triazolyl (wobei die genannten Hetaryle gegebenenfalls selbst durch C1-C4-Alkyl oder Halogen substituiert sind) substituiertes C3-C6-Cycloalkyl-C1-C4-alkyl, gegebenenfalls durch Halogen, Cyano (auch im C1-C4-Alkylteil von Heterocyclyl-C1-C4-alkyl), Nitro, Hydroxy, C1-C4-Alkyl, C1-C4-Halogenalkyl, C3-C6-Cycloalkyl (welches gegebenenfalls durch Halogen, Cyano, C1-C4-Alkyl und C3-C6-Cycloalkyl substituiert ist), C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C1-C4-Alkylthio, C1-C4-Halogenalkylthio, C1-C4-Alkylsulfinyl, C1-C4-Alkylsulfonyl, C1-C4-Halogenalkylsulfinyl, C1-C4-Halogenalkylsulfonyl, Amino, C1-C4-Alkylamino, Di-(C1-C4-alkyl)-amino, C1-C4-Alkylcarbonylamino, C1-C4-Alkoxycarbonylamino, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4-Halogenalkoxy-C1-C4-alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl-C1-C4-alkyl, C1-C4-Alkylcarbonyl, C1-C4-Alkoxycarbonyl oder Aminocarbonyl substituiertes Heterocyclyl-C1-C4-alkyl, gegebenenfalls durch Halogen, Cyano, Nitro, Hydroxy, Amino, C1-C4-Alkyl, C1-C4-Halogenalkyl, C3-C6-Cycloalkyl (welches gegebenenfalls durch Halogen, Cyano, C1-C4-Alkyl und C3-C6-Cycloalkyl substituiert ist), C1-C4-Alkoxy oder C1-C4-Halogenalkoxy substituiertes Aryl, gegebenenfalls durch Halogen, Cyano (auch im C1-C4-Alkylteil von Aryl-C1-C4-alkyl), Nitro, Hydroxy, Amino, C1-C4-Alkyl, C1-C4-Halogenalkyl, C3-C6-Cycloalkyl (welches gegebenenfalls durch Halogen, Cyano, C1-C4-Alkyl und C3-C6-Cycloalkyl substituiert ist), C1-C4-Alkoxy oder C1-C4-Halogenalkoxy substituiertes Aryl-C1-C4-alkyl, gegebenenfalls durch Halogen, Cyano (auch im C1-C4-Alkylteil von Hetaryl-C1-C4-alkyl), Nitro, Hydroxy, C1-C4-Alkyl, C1-C4-Halogenalkyl, C3-C6-Cycloalkyl (welches gegebenenfalls durch Halogen, Cyano, C1-C4-Alkyl und C3-C6-Cycloalkyl substituiert ist), C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C1-C4-Alkylthio, C1-C4-Halogenalkylthio, C1-C4-Alkylsulfinyl, C1-C4-Alkylsulfonyl, C1-C4-Halogenalkylsulfinyl, C1-C4-Halogenalkylsulfonyl, Amino, C1-C4-Alkylamino, Di-(C1-C4-alkyl)-amino, C1-C4-Alkylcarbonylamino, C1-C4-Alkoxycarbonylamino, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4-Halogenalkoxy-C1-C4-alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl-C1-C4-alkyl, C1-C4-Alkylcarbonyl, C1-C4-Alkoxycarbonyl oder Aminocarbonyl substituiertes Hetaryl-C1-C4-alkyl, oder
R22
für einen D-Rest aus der Reihe (D-1) bis (D-3)
Figure imgb0169
 oder für einen der folgenden E-Reste
Figure imgb0170
Figure imgb0171
Figure imgb0172
Figure imgb0173
Figure imgb0174
 steht, oder, im Fall R2 = d),
R22
auch für den Rest (E-13)
Figure imgb0175
 steht,
R23
für einen Rest aus der Reihe Wasserstoff, C1-C6-Alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkenyl, C1-C6-Alkoxy, C2-C6-Alkenyloxy, C2-C6-Alkinyloxy, C3-C6-Cycloalkyloxy, C1-C4-Alkylthio-C1-C4-alkyl, C2-C4-Alkenylthio-C1-C4-alkyl, Cyano-C1-C4-alkyl und C1-C4-Alkoxy-C1-C4 -alkyl steht,
oder, für R2 = c) oder g),
R22 und R23
gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen gesättigten vier- bis sechsgliedrigen Ring bilden, der ein weiteres Heteroatome aus der Reihe Stickstoff, Sauerstoff und Schwefel enthalten kann,
R26
für einen Rest aus der Reihe Wasserstoff, C1-C4-Alkyl, C1-C4-Halogenalkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C4-alkyl, C1-C4-Alkoxy-C1-C2-alkyl, C1-C4-Alkylsulfanyl, C1-C4-Halogenalkylsulfanyl, C1-C4-Alkylsulfinyl, C1-C4-Halogenalkylsulfinyl, C1-C4-Alkylsulfonyl, C1-C4-Alkylthio-C1-C2-alkyl, C1-C4-Alkylsulfinyl-C1-C2-alkyl, C1-C4-Alkylsulfonyl-C1-C2-alkyl und Cyano-C1-C4-alkyl steht und
R27
für Wasserstoff, C1-C4-Alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C4-alkyl, C1-C4-Alkoxy-C1-C2-alkyl, C1-C4-Alkylthio-C1-C2-alkyl, C1-C4-Alkylsulfinyl-C1-C2-alkyl, C1-C4-Alkylsulfonyl-C1-C2-alkyl oder Cyano-C1-C4-alkyl steht und
Verbindungen der Formel (I), worin
A
für den A-Rest
Figure imgb0176
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet,
G1
für N oder C-B1 steht,
B1
für einen Rest aus der Reihe Wasserstoff, Halogen, C1-C6-Alkyl und C1-C4-Halogenalkyl steht,
B2
für einen Rest aus der Reihe Wasserstoff, Halogen, C1-C6-Alkyl und C1-C4-Halogenalkyl steht,
T
für Sauerstoff oder ein Elektronenpaar steht,
Q
für Schwefel steht,
R1
für einen Rest aus der Reihe Wasserstoff, C1-C4-Alkyl und C1-C4-Alkoxy steht,
R2
a) für einen B-Rest aus der Reihe
Figure imgb0177
Figure imgb0178
Figure imgb0179
Figure imgb0180
Figure imgb0181
Figure imgb0182
Figure imgb0183
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder
R2
c) für einen Rest der Formel
Figure imgb0184
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder
R2
d) für einen Rest der Formel
Figure imgb0185
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder
R2
e) für einen F-Rest aus der Reihe (F-8) und (F-10)
Figure imgb0186
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom in der Formel (I) bedeutet, oder
R2
f) für einen Rest aus der Reihe C1-C6-Halogenalkyl und Carboxyl steht,
R2
g) für einen Rest der Formel
Figure imgb0187
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, worin
G2
für Wasserstoff oder einen Rest aus der Reihe Halogen, Nitro, Amino, Cyano, C1-C4-Alkylamino, Halogen-C1-C4-Alkylamino, Di-(C1-C4-alkyl)-amino, C1-C4-Alkyl, Halogen-C1-C4-alkyl, C1-C4-Alkoxy, Halogen-C1-C4-alkoxy, C1-C4-Alkoxy-C1-C4-alkyl, halogeniertes C1-C4-Alkoxy-C1-C4-alkyl, Bis(C1-C4-alkoxy)-C1-C4-alkyl, Bis(halogen-C1-C4-alkoxy)-C1-C4-alkyl, C1-C4-Alkoxy-(C1-C4-alkylsulfanyl)-C1-C4-alkyl, C1-C4-Alkoxy-(C1-C4-alkylsulfinyl)-C1-C4-alkyl, C1-C4-Alkoxy-(C1-C4-alkylsulfonyl)-C1-C4-alkyl, Bis(C1-C4-alkylsulfanyl)-C1-C4-alkyl, Bis(halogen-C1-C4-alkylsulfanyl)-C1-C4-alkyl, Bis(hydroxy-C1-C4-alkylsulfanyl)-C1-C4-alkyl, C1-C4-Alkoxycarbonyl, C1-C4-Alkoxycarbonyl-C1-C4-alkyl, C(X2)NR3R4, NR6R7, C1-C4-Alkylthio, C1-C4-Alkylsulfinyl, C1-C4-Alkylsulfonyl, C1-C4-Halogenalkylthio, C1-C4-Halogenalkylsulfinyl, C1-C4-Halogenalkylsulfonyl, die Heterocyclylreste Dioxanyl, Dioxolanyl, Dioxepanyl, Dioxocanyl, Oxathianyl, Oxathiolanyl, Oxathiepanyl, Oxathiocanyl, Dithianyl, Dithiolanyl, Dithiepanyl, Dithiocanyl, Oxathianyloxid, Oxathiolanyloxid, Oxathiepanyloxid, Oxathiocanyloxid, Oxathianyldioxid, Oxathiolanyldioxid, Oxathiepanyldioxid, Oxathiocanyldioxid, Morpholinyl, Triazolinonyl, Oxazolinyl, Dihydrooxadiazinyl, Dihydrodioxazinyl, Dihydrooxazolyl, Dihydrooxazinyl und Pyrazolinonyl (welche selbst wiederum substituiert sein können durch C1-C4-Alkyl, Halogen-C1-C4-alkyl, C1-C4-Alkoxy und C1-C4-Alkoxy-C1-C4-alkyl), Phenyl (welches selbst wiederum substituiert sein kann durch Halogen, Cyano, Nitro, C1-C4-Alkyl und Halogen-C1-C4-alkyl), die Heteroarylreste Pyridyl, Pyridyl-N-oxid, Pyrimidyl, Imidazolyl, Pyrazolyl, Oxazolyl, Thiazolyl, Furanyl, Thienyl, Triazolyl, Tetrazolyl, Oxadiazolyl, Thiadiazolyl, Pyrazinyl, Triazinyl, Tetrazinyl und Isochinolinyl (welche selbst wiederum substituiert sein können durch Halogen, Nitro, C1-C4-Alkyl, Halogen-C1-C4-alkyl, C1-C4-Alkoxy, Halogen-C1-C4-alkoxy, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4-Alkylthio, C1-C4-Alkylthio-C1-C4-alkyl und C3-C6-Cycloalkyl) und die Heteroaryl-C1-C4-alkylreste Triazolyl-C1-C4-alkyl, Pyridyl-C1-C4-alkyl, Pyrimidyl-C1-C4-alkyl und Oxadiazolyl-C1-C4-alkyl (welche selbst wiederum substituiert sein können durch Halogen und C1-C4-Alkyl), oder
G2
für einen C-Rest aus der Reihe (C-1), (C-6) und (C-9)
Figure imgb0188
 steht, worin die gestrichelte Linie die Bindung zu den B-Resten bedeutet,
X
für Sauerstoff steht,
X2
für Sauerstoff, Schwefel, NR5 oder NOH steht,
n
für 2 steht,
R3
für C1-C4-Alkyl steht,
R4
für einen Rest aus der Reihe Wasserstoff, C1-C4-Alkyl, Halogen-C1-C4-alkyl, Cyano-C1-C4-alkyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C4-alkyl, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4-Alkoxycarbonyl, C1-C4-Alkoxycarbonyl-C1-C4-alkyl und C1-C4-Alkylthio-C1-C4-alkyl steht,
R5
für einen Rest aus der Reihe Wasserstoff, C1-C4-Alkyl, Halogen-C1-C4-alkyl, Cyano-C1-C4-alkyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C4-alkyl, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4-Alkoxycarbonyl, C1-C4-Alkoxycarbonyl-C1-C4-alkyl und C1-C4-Alkylthio-C1-C4-alkyl steht,
R6
für Wasserstoff oder C1-C4-Alkyl steht,
R7
für einen Rest aus der Reihe Wasserstoff, C1-C4-Alkyl, Halogen-C1-C4-alkyl, Cyano-C1-C4-alkyl, C2-C4-Alkinyl, C1-C4-Alkoxy, Halogen-C1-C4-alkoxy, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4-Alkoxycarbonyl, C1-C4-Alkoxycarbonyl-C1-C4-alkyl, C1-C4-Alkylthio-C1-C4-alkyl, Aryl-C1-C4-alkyl oder Hetaryl-C1-C4-alkyl steht, oder
R6 und R7
gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen 4- bis 7-gliedrigen Ring bilden, der ein oder zwei weitere Heteroatome aus der Reihe Stickstoff, Sauerstoff und Schwefel (wobei Sauerstoff- und Schwefelatome nicht unmittelbar benachbart sein dürfen) enthalten kann,
R8
für einen Rest aus der Reihe Wasserstoff, C1-C6-Alkyl, C1-C6-Halogenalkyl, Cyano-C1-C6-alkyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C2-C6-Alkenyl, C1-C6-Alkoxy-C1-C6-alkyl, jeweils gegebenenfalls durch Halogen substituiertes C1-C6-Alkylcarbonyl und C1-C6-Alkylsulfonyl, gegebenenfalls durch Halogen substituiertes C1-C6-Alkoxycarbonyl und gegebenenfalls durch Halogen, C1-C6-Alkyl, C1-C6-Alkoxy, C1-C6-Halogenalkyl und Cyano substituiertes C3-C6-Cycloalkylcarbonyl steht, oder für ein Kation oder ein gegebenenfalls durch C1-C6-Alkyl oder Aryl-C1-C6-alkyl substituiertes Ammonium-Ion steht,
R9
für einen Rest aus der Reihe jeweils gegebenenfalls durch Halogen, C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C1-C4-Alkylthio, C1-C4-Halogenalkylthio, C1-C4-Alkylsulfinyl, C1-C4-Halogenalkylsulfinyl, C1-C4-Alkylsulfonyl und C1-C4-Halogenalkylsulfonyl substituiertes C1-C4-Alkyl, C2-C4-Alkenyl und C2-C4-Alkinyl, jeweils gegebenenfalls durch Halogen, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy substituiertes C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C4-alkyl und C3-C4-Cycloalkenyl, in welchen ein oder zwei Ringglieder jeweils durch ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff ersetzt sein können (und dabei insbesondere für
Figure imgb0189
 wobei der Pfeil jeweils die Bindung zum S-Atom in dem Rest (C-1) markiert), jeweils gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, C1-C4-Alkyl, C1-C4-Halogenalkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C1-C4-Alkylthio, C1-C4-Halogenalkylthio, C1-C4-Alkylsulfinyl, C1-C4-Halogenalkylsulfinyl, C1-C4-Alkylsulfonyl, C1-C4-Halogenalkylsulfonyl, Amino, C1-C4-Alkylamino, Di-(C1-C4-alkyl)-amino, C1-C4-Alkylcarbonylamino, C1-C4-Alkoxycarbonylamino, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4-Halogenalkoxy-C1-C4-alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl-C1-C4-alkyl, C1-C4-Alkylcarbonyl, C1-C4-Alkoxycarbonyl oder Aminocarbonyl substituiertes Aryl, Heteroaryl, Aryl-C1-C4-alkyl und Heteroaryl-C1-C4-alkyl oder für NR'R" steht, worin R' und R" unabhängig voneinander für einen Rest aus der Reihe Wasserstoff und C1-C4-Alkyl stehen, oder
R8 und R9
können im Rest (C-1) auch zusammen mit der N-S(O)n Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls durch Halogen, C1-C6-Alkyl, C1-C6-Halogenalkyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy substituierten 5- bis 7-gliedrigen Ring bilden, der ein oder zwei Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine und bevorzugt genau eine Carbonylgruppe enthalten kann, insbesondere können R8 und R9 zusammen mit der N-S(O)n Gruppe, an die sie gebunden sind, für einen Rest aus der Reihe
Figure imgb0190
Figure imgb0191
 stehen (worin der Pfeil jeweils die Bindung zur C(X)-Gruppe markiert),
R15
für einen Rest aus der Reihe jeweils gegebenenfalls durch Methyl substituiertes C1-C6-Alkyl, C2-C6-Alkenyl und C2-C6-Alkinyl und jeweils gegebenenfalls durch Methyl, Halogen, Cyano oder Carbamoyl substituiertes C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C2-alkyl und C3-C6-Cycloalkenyl steht,
R8 und R15
im Rest (C-6) auch zusammen mit der N-S(O)n-Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls substituierten 4- bis 8-gliedrigen Ring bilden können, der ein oder zwei weitere Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoff- und Schwefelatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine Carbonylgruppe enthalten kann,
R17
für einen Rest aus der Reihe jeweils gegebenenfalls durch Halogen, C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C1-C4-Alkylthio, C1-C4-Halogenalkylthio, C1-C4-Alkylsulfinyl, C1-C4-Halogenalkylsulfinyl, C1-C4-Alkylsulfonyl und C1-C4-Halogenalkylsulfonyl substituiertes C1-C4-Alkyl, C2-C4-Alkenyl und C2-C4-Alkinyl, jeweils gegebenenfalls durch Halogen, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy substituiertes C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C4-alkyl, C3-C4-Cycloalkenyl, N-Pyrrolidinyl, N-Piperidinyl, N-Morpholinyl, N-Thiomorpholinyl, N-Thiomorpholinyl-1-oxid, N-Thiomorpholinyl-1,1-dioxid, N-Piperazinyl, N-1-Methylpiperazinyl und N-2-Oxo-1-methylpiperazinyl, jeweils gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, C1-C4-Alkyl, C1-C4-Halogenalkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C1-C4-Alkylthio, C1-C4-Halogenalkylthio, C1-C4-Alkylsulfinyl, C1-C4-Halogenalkylsulfinyl, C1-C4-Alkylsulfonyl, C1-C4-Halogenalkylsulfonyl, Amino, C1-C4-Alkylamino, Di-(C1-C4-alkyl)-amino, C1-C4-Alkylcarbonylamino, C1-C4-Alkoxycarbonylamino, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4-Halogenalkoxy-C1-C4-alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl-C1-C4-alkyl, C1-C4-Alkylcarbonyl, C1-C4-Alkoxycarbonyl oder Aminocarbonyl substituiertes Aryl, Heteroaryl, Aryl-C1-C4-alkyl und Heteroaryl-C1-C4-alkyl oder für NR'R"steht, worin R' und R" unabhängig voneinander für einen Rest aus der Reihe Wasserstoff und C1-C4-Alkyl stehen, und im Fall, dass R2 für g) steht,
R22
für einen Rest aus der Reihe Wasserstoff, C1-C4-Alkyl, C2-C4-Halogenalkyl, Cyano-C1-C4-alkyl, C2-C4-Alkenyl, C2-C4-Halogenalkenyl, C2-C4-Alkinyl, C2-C4-Halogenalkinyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy, gegebenenfalls durch Halogen substituiertes C1-C2-Alkoxy-C1-C4-alkyl, gegebenenfalls durch Halogen substituiertes Bis(C1-C2-alkoxy)-C1-C4-alkyl, gegebenenfalls durch Halogen substituiertes C1-C4-Alkylsulfanyl-C1-C4-alkyl, gegebenenfalls durch Halogen substituiertes C1-C4-Alkylcarbonyl-C1-C4-alkyl, gegebenenfalls durch Halogen substituiertes C1-C4-Alkylsulfinyl-C1-C4-alkyl, gegebenenfalls durch Halogen substituiertes C1-C4-Alkylsulfonyl-C1-C4-alkyl, Di-(C1-C4-alkyl)-aminosulfanyl-C1-C4-alkyl, Di-(C1-C4-alkyl)-aminosulfinyl-C1-C4-alkyl, Di-(C1-C4-alkyl)-aminosulfonyl-C1-C4-alkyl, gegebenenfalls durch Halogen substituiertes C1-C4-Alkoxycarbonyl, gegebenenfalls durch Halogen substituiertes C1-C4-Alkoxycarbonyl-C1-C4-alkyl, gegebenenfalls durch Halogen substituiertes C2-C4-Alkinyloxy, gegebenenfalls durch Halogen substituiertes C2-C4-Alkinyloxycarbonyl, Di-(C1-C4-alkyl)-aminocarbonyl, N-C1-C4-Alkyl-N-C3-C6-cycloalkylaminocarbonyl, Di-(C1-C4-alkyl)-aminocarbonyl-C1-C4-alkyl, N-C1-C4-Alkyl-N-C3-C6-cycloalkylaminocarbonyl-C1-C4-alkyl, Heterocyclylcarbonyl-C1-C4-alkyl, C1-C4-Alkylsulfanyl, C1-C4-Halogenalkylsulfanyl, C1-C4-Alkylsulfinyl, C1-C4-Halogenalkylsulfinyl, C1-C4-Alkylsulfonyl, C1-C4-Halogenalkylsulfonyl, gegebenenfalls durch Halogen, Cyano, Nitro, C1-C4-Alkyl, C1-C4-Halogenalkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C1-C4-Alkoxycarbonyl, C1-C4-Halogenalkoxycarbonyl oder Pyridyl (welches gegebenenfalls selbst durch C1-C4-Alkyl oder Halogen substituiert ist) substituiertes C3-C6-Cycloalkyl, gegebenenfalls durch Halogen, Cyano, Nitro, C1-C4-Alkyl, C1-C4-Halogenalkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C1-C4-Alkoxycarbonyl, C1-C4-Halogenalkoxycarbonyl oder Pyridyl (welches gegebenenfalls selbst durch C1-C4-Alkyl oder Halogen substituiert ist) substituiertes C3-C6-Cycloalkylcarbonyl, gegebenenfalls durch Halogen, Cyano, Nitro, C1-C4-Alkyl, C1-C4-Halogenalkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C1-C4-Alkoxycarbonyl, C1-C4-Halogenalkoxycarbonyl, Pyridyl, Pyrimidyl, Pyrazanyl, Pyridazinyl, Thiazolyl, Isothiazolyl, Thiadiazolyl, Oxazolyl, Isoxazolyl, Oxadiazolyl, Pyrazolyl, Triazinyl oder Triazolyl (wobei die genannten Hetaryle gegebenenfalls selbst durch C1-C4-Alkyl oder Halogen substituiert sind) substituiertes C3-C6-Cycloalkyl-C1-C4-alkyl, gegebenenfalls durch Halogen, Cyano (auch im C1-C4-Alkylteil von Heterocyclyl-C1-C4-alkyl), Nitro, Hydroxy, C1-C4-Alkyl, C1-C4-Halogenalkyl, C3-C6-Cycloalkyl (welches gegebenenfalls durch Halogen, Cyano, C1-C4-Alkyl und C3-C6-Cycloalkyl substituiert ist), C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C1-C4-Alkylthio, C1-C4-Halogenalkylthio, C1-C4-Alkylsulfinyl, C1-C4-Alkylsulfonyl, C1-C4-Halogenalkylsulfinyl, C1-C4-Halogenalkylsulfonyl, Amino, C1-C4-Alkylamino, Di-(C1-C4-alkyl)-amino, C1-C4-Alkylcarbonylamino, C1-C4-Alkoxycarbonylamino, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4-Halogenalkoxy-C1-C4-alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl-C1-C4-alkyl, C1-C4-Alkylcarbonyl, C1-C4-Alkoxycarbonyl oder Aminocarbonyl substituiertes Heterocyclyl-C1-C4-alkyl, gegebenenfalls durch Halogen, Cyano, Nitro, Hydroxy, Amino, C1-C4-Alkyl, C1-C4-Halogenalkyl, C3-C6-Cycloalkyl (welches gegebenenfalls durch Halogen, Cyano, C1-C4-Alkyl und C3-C6-Cycloalkyl substituiert ist), C1-C4-Alkoxy oder C1-C4-Halogenalkoxy substituiertes Aryl, gegebenenfalls durch Halogen, Cyano (auch im C1-C4-Alkylteil von Aryl-C1-C4-alkyl), Nitro, Hydroxy, Amino, C1-C4-Alkyl, C1-C4-Halogenalkyl, C3-C6-Cycloalkyl (welches gegebenenfalls durch Halogen, Cyano, C1-C4-Alkyl und C3-C6-Cycloalkyl substituiert ist), C1-C4-Alkoxy oder C1-C4-Halogenalkoxy substituiertes Aryl-C1-C4-alkyl, gegebenenfalls durch Halogen, Cyano (auch im C1-C4-Alkylteil von Hetaryl-C1-C4-alkyl), Nitro, Hydroxy, C1-C4-Alkyl, C1-C4-Halogenalkyl, C3-C6-Cycloalkyl (welches gegebenenfalls durch Halogen, Cyano, C1-C4-Alkyl und C3-C6-Cycloalkyl substituiert ist), C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C1-C4-Alkylthio, C1-C4-Halogenalkylthio, C1-C4-Alkylsulfinyl, C1-C4-Alkylsulfonyl, C1-C4-Halogenalkylsulfinyl, C1-C4-Halogenalkylsulfonyl, Amino, C1-C4-Alkylamino, Di-(C1-C4-alkyl)-amino, C1-C4-Alkylcarbonylamino, C1-C4-Alkoxycarbonylamino, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4-Halogenalkoxy-C1-C4-alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl-C1-C4-alkyl, C1-C4-Alkylcarbonyl, C1-C4-Alkoxycarbonyl oder Aminocarbonyl substituiertes Hetaryl-C1-C4-alkyl steht, und im Fall, dass R2 für g) steht,
R22
für einen D-Rest aus der Reihe (D-1) bis (D-3)
Figure imgb0192
 worin
X1
für einen Rest aus der Reihe Wasserstoff, Fluor, Chlor, Brom, Jod, Cyano, Nitro, C1-C4-Alkyl, C1-C4-Halogenalkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy und C1-C4-Halogenalkoxy steht,
R
für NR18R19 oder für jeweils gegebenfalls einfach bis siebenfach durch Halogen, einfach oder zweifach durch Sauerstoff (führt zu C=O) oder einfach oder zweifach durch Cyano substituiertes C1-C6-Alkyl, C3-C6-Alkenyl, C3-C6-Alkinyl, C1-C4-Alkoxy-C1-C3-alkyl, C1-C4-Alkyl-S-C1-C3-alkyl, C1-C4-Alkyl-S(O)-C1-C3-alkyl, C1-C4-Alkyl-S(O)2-C1-C3-alkyl, für R18-CO-C1-C2-alkyl, für NR18R19-CO-C1-C2-alkyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=O), C1-C4-Alkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy und C1-C4-Halogenalkyl substituiertes C3-C6-Cycloalkyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=O), C1-C4-Alkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy und C1-C4-Halogenalkyl substituiertes C3-C8-Cycloalkenyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=O), C1-C4-Alkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy und C1-C4-Halogenalkyl substituiertes C3-C6-Cycloalkyl-C1-C4-alkyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=O), C1-C4-Alkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy und C1-C4-Halogenalkyl substituiertes C3-C6-Cycloalkenyl-C1-C4-alkyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=O), C1-C4-Alkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy und C1-C4-Halogenalkyl substituiertes Heterocyclyl, für gegebenenfalls einfach oder zweifach durch Sauerstoff (führt zu C=O), C1-C4-Alkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy und C1-C4-Halogenalkyl substituiertes Heterocyclyl-Ci-C4-alkyl oder für jeweils gegebenenfalls einfach bis dreifach durch Halogen, Cyano, C1-C4-Alkyl, C1-C4-Halogenalkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy oder C1-C4-Halogenalkoxy substituiertes Phenyl, Phenyl-C1-C4-alkyl, Hetaryl und Hetaryl-C1-C4-alkyl steht,
Y3
für einen Rest aus der Reihe Wasserstoff, Fluor, Chlor, Brom, Jod, Cyano, C1-C4-Alkyl, C1-C4-Halogenalkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy und C1-C4-Halogenalkoxy steht,
W
für einen Rest aus der Reihe S, SO und SO2 steht,
R22
ferner für einen der folgenden E-Reste
Figure imgb0193
Figure imgb0194
Figure imgb0195
Figure imgb0196
Figure imgb0197
 steht, oder, im Fall R2 = d),
R22
auch für den Rest (E-13)
Figure imgb0198
 steht,
R18
für einen Rest aus der Reihe Wasserstoff, Hydroxy, jeweils gegebenenfalls einfach oder mehrfach durch Halogen oder einfach oder zweifach durch Cyano substituiertes C1-C4-Alkyl, C1-C4-Alkoxy, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4-Alkyl-S-C1-C3-alkyl, C1-C4-Alkyl-S(O)-C1-C3-alkyl, C1-C4-Alkyl-S(O)2-C1-C3-alkyl, C1-C4-Alkylcarbonyl, C1-C4-Alkoxycarbonyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C3-alkyl, Heterocyclyl, Heterocyclyl-C1-C3-alkyl und jeweils gegebenenfalls einfach bis dreifach durch C1-C4-Alkyl, C1-C3-Halogenalkyl, C1-C3-Alkoxy, C1-C3-Halogenalkoxy, Cyclopropyl, Fluor Chlor, Brom oder Cyano substituiertes Phenyl, Benzyl, Pyridyl, Pyrimidyl, Thiazolyl, Oxazolyl, Pyrazolyl, Thienyl, Furanyl, Pyridinylmethyl und Thiazolylmethyl steht,
R19
für Wasserstoff, für ein Alkali- oder Erdalkalimetallion, für ein gegebenfalls einfach bis vierfach durch C1-C4-Alkyl substituiertes Ammoniumion oder für einen jeweils gegebenenfalls einfach oder mehrfach durch Halogen oder einfach oder zweifach durch Cyano substituierten Rest aus der Reihe C1-C4-Alkyl, C1-C4-Alkoxy, C1-C4-Alkoxy-C1-C2-alkyl, C1-C4-Alkyl-S-C1-C2-alkyl, C1-C4-Alkyl-S(O)-C1-C2-alkyl und C1-C4-Alkyl-S(O)2-C1-C2-alkyl steht,
R23
für einen Rest aus der Reihe Wasserstoff, C1-C6-Alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkenyl, C1-C6-Alkoxy, C2-C6-Alkenyloxy, C2-C6-Alkinyloxy, C3-C6-Cycloalkyloxy, C1-C4-Alkylthio-C1-C4-alkyl, C2-C4-Alkenylthio-C1-C4-alkyl, Cyano-C1-C4-alkyl und C1-C4-Alkoxy-C1-C4-alkyl steht,
oder, für R2 = g),
R22 und R23
gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen gesättigten vier- bis sechsgliedrigen Ring bilden, der ein weiteres Heteroatome aus der Reihe Stickstoff, Sauerstoff und Schwefel enthalten kann,
R26
für einen Rest aus der Reihe Wasserstoff, C1-C4-Alkyl, C1-C4-Halogenalkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C4-alkyl, C1-C4-Alkoxy-C1-C2-alkyl, C1-C4-Alkylsulfanyl, C1-C4-Halogenalkylsulfanyl, C1-C4-Alkylsulfinyl, C1-C4-Halogenalkylsulfinyl, C1-C4-Alkylsulfonyl, C1-C4-Alkylthio-C1-C2-alkyl, C1-C4-Alkylsulfinyl-C1-C2-alkyl, C1-C4-Alkylsulfonyl-C1-C2-alkyl und Cyano-C1-C4-alkyl steht und
R27
für Wasserstoff, C1-C4-Alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C4-alkyl, C1-C4-Alkoxy-C1-C2-alkyl, C1-C4-Alkylthio-C1-C2-alkyl, C1-C4-Alkylsulfinyl-C1-C2-alkyl, C1-C4-Alkylsulfonyl-C1-C2-alkyl oder Cyano-C1-C4-alkyl steht.
Preferred range (2): Particular preference is given to compounds of the formula (I) in which
A
for an A-residue from the series (Ab) and (Af)
Figure imgb0152
 in which the dashed line denotes the bond to the carbon atom of the bicyclic compound of the formula (I),
B 2
a radical selected from the group consisting of hydrogen, halogen, C 1 -C 6 -alkyl and C 1 -C 4 -haloalkyl,
Q
stands for sulfur,
R 1
a radical selected from the group consisting of hydrogen, C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy,
R 2
a) for a B residue from the series
Figure imgb0153
Figure imgb0154
Figure imgb0155
Figure imgb0156
Figure imgb0157
Figure imgb0158
Figure imgb0159
 wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R 2
b) for a D radical from the series (D-1) to (D-3)
Figure imgb0160
 wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R 2
c) a radical of the formula
Figure imgb0161
 wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R 2
d) for a radical of the formula
Figure imgb0162
 wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R 2
e) for an F radical from the series (F-1), (F-8) and (F-10)
Figure imgb0163
 wherein the dashed line represents the bond to the carbon atom in the formula (I), or
R 2
f) is a radical from the series C 1 -C 6 -haloalkyl and carboxyl,
R 2
g) for a radical of the formula
Figure imgb0164
 wherein the dotted line represents the bond to the carbon atom of the bicyclic moiety of formula (I) wherein
G 2
is hydrogen or a radical selected from halogen, nitro, amino, cyano, C 1 -C 4 -alkylamino, halo-C 1 -C 4 -alkylamino, di- (C 1 -C 4 -alkyl) -amino, C 1 C 4 alkyl, halo C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halo C 1 -C 4 alkoxy, C 1 -C 4 alkoxy-C 1 -C 4 alkyl, halogenated C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, bis (C 1 -C 4 -alkoxy) C 1 -C 4 -alkyl, bis (halogeno-C 1 -C 4 -alkoxy) -C C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy- (C 1 -C 4 -alkylsulfanyl) C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy- (C 1 -C 4 -alkylsulfinyl) C 1 -C 4 alkyl, C 1 -C 4 alkoxy (C 1 -C 4 alkylsulfonyl) C 1 -C 4 alkyl, bis (C 1 -C 4 alkylsulfanyl) C 1 -C 4- alkyl, bis (halo-C 1 -C 4 alkylsulfanyl) C 1 -C 4 alkyl, bis (hydroxy C 1 -C 4 alkylsulfanyl) C 1 -C 4 alkyl, C 1 -C 4- alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl, C (X 2 ) NR 3 R 4 , NR 6 R 7 , C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfinyl , C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -haloalkylsulfone yl, which heterocyclyl dioxanyl, dioxolanyl, dioxepanyl, Dioxocanyl, Oxathianyl, Oxathiolanyl, Oxathiepanyl, Oxathiocanyl, dithianyl, dithiolanyl, Dithiepanyl, Dithiocanyl, Oxathianyloxid, Oxathiolanyloxid, Oxathiepanyloxid, Oxathiocanyloxid, Oxathianyldioxid, Oxathiolanyldioxid, Oxathiepanyldioxid, Oxathiocanyldioxid, morpholinyl, Triazolinonyl, oxazolinyl, Dihydrooxadiazinyl, dihydrodioxazinyl, dihydrooxazolyl, dihydrooxazinyl and pyrazolinonyl (which in turn may be substituted by C 1 -C 4 alkyl, halo-C 1 -C 4 alkyl, C 1 -C 4 alkoxy and C 1 -C 4 alkoxy C 1 -C 4 -alkyl), phenyl (which in turn may itself be substituted by halogen, cyano, nitro, C 1 -C 4 -alkyl and halogeno-C 1 -C 4 -alkyl), the heteroaryl radicals pyridyl, pyridyl- N- oxide, pyrimidyl, imidazolyl, pyrazolyl, Oxazolyl, thiazolyl, furanyl, thienyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyrazinyl, triazinyl, tetrazinyl and isoquinolinyl (which themselves may be substituted by halo, nitro, C 1 -C 4 alkyl, haloC 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halo-C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio, C 1 -C 4 Alkylthio-C 1 -C 4 -alkyl and C 3 -C 6 -cycloalkyl) and the heteroaryl-C 1 -C 4 -alkyl radicals triazolyl-C 1 -C 4 -alkyl, pyridyl-C 1 -C 4 -alkyl, Pyrimidyl-C 1 -C 4 -alkyl and oxadiazolyl-C 1 -C 4 -alkyl (which in turn may themselves be substituted by halogen and C 1 -C 4 -alkyl), or
G 2
for a C-residue from the series (C-1), (C-6) and (C-9)
Figure imgb0165
 wherein the dashed line indicates the bond to the B radicals,
X
stands for oxygen,
X 1
a radical selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 - Alkoxy and C 1 -C 4 -haloalkoxy,
X 2
is oxygen, sulfur, NR 5 or NOH,
n
stands for 2,
R
for NR 18 R 19 or for any monosubstituted to trisubstituted by halogen, monosubstituted or disubstituted by oxygen (leads to C = O) or mono- or disubstituted by cyano-substituted C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 1 -C 4 -alkoxy-C 1 -C 3 -alkyl, C 1 -C 4 -alkyl-SC 1 -C 3 -alkyl, C 1 -C 4 -alkyl-S ( O) -C 1 -C 3 -alkyl, C 1 -C 4 -alkyl-S (O) 2 -C 1 -C 3 -alkyl, for R 18 -CO-C 1 -C 2 -alkyl, for NR 18 R 19 -CO-C 1 -C 2 -alkyl, optionally optionally mono- or disubstituted by oxygen (leads to C = O), C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 - Alkoxy and C 1 -C 4 -haloalkyl substituted C 3 -C 6 -cycloalkyl, optionally substituted once or twice by oxygen (leads to C = O), C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkyl-substituted C 3 -C 8 -cycloalkenyl, optionally substituted once or twice by oxygen (leads to C = O), C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkyl-substituted C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, optionally optionally mono- or disubstituted by oxygen (leads to C = O), C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkyl-substituted C 3 -C 6 -cycloalkenyl-C 1 -C 4 -alkyl, optionally substituted once or twice by oxygen (leads to C = O), C 1 C 4 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy and C 1 -C 4 haloalkyl substituted heterocyclyl, optionally substituted once or twice by oxygen (leads to C = O), C 1 - C 4 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy and C 1 -C 4 -halogenoalkyl-substituted heterocyclyl-Ci-C4-alkyl or represents in each case optionally mono- to trisubstituted by halogen, cyano, C 1 -C 4 - Alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy-substituted phenyl, phenyl-C 1 -C 4 -alkyl, hetaryl and hetaryl- C 1 -C 4 -alkyl,
R 3
is C 1 -C 4 -alkyl,
R 4
a radical selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 2 -C 4 -alkynyl, C 3 -C 6 - Cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl- C 1 -C 4 -alkyl and C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl,
R 5
a radical selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 2 -C 4 -alkynyl, C 3 -C 6 - Cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl- C 1 -C 4 -alkyl and C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl,
R 6
is hydrogen or C 1 -C 4 -alkyl,
R 7
a radical selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 2 -C 4 -alkynyl, C 1 -C 4 - Alkoxy, halo-C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 - alkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, aryl-C 1 -C 4 -alkyl or hetaryl-C 1 -C 4 -alkyl, or
R 6 and R 7
together with the nitrogen atom to which they are attached form a 4- to 7-membered ring which may contain one or two further nitrogen, oxygen and sulfur heteroatoms (oxygen and sulfur atoms not being immediately adjacent);
R 8
a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, cyano-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, in each case optionally halogen-substituted C 1 -C 6 -alkylcarbonyl and C 1 -C 6 -alkylsulfonyl, optionally C-substituted by halogen C 1 -C 6 -alkoxycarbonyl and optionally substituted by halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkyl and cyano-substituted C 3 -C 6 -cycloalkylcarbonyl, or a cation or an ammonium ion which is optionally substituted by C 1 -C 6 -alkyl or aryl-C 1 -C 6 -alkyl,
R 9
in each case a halogen radical, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfinyl , C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl and C 1 -C 4 -haloalkylsulfonyl-substituted C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl and C 2 -C 4 -alkynyl, respectively C 3 -C 6 -cycloalkyl optionally substituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 3 -C 6 - Cycloalkyl-C 1 -C 4 -alkyl and C 3 -C 4 -cycloalkenyl in which one or two ring members each by a heteroatom from the series sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen may be replaced (and in particular for
Figure imgb0166
 wherein the arrow in each case marks the bond to the S atom in the radical (C-1) and in the radical (F-1)), in each case optionally by halogen, cyano (also in the alkyl part), nitro, C 1 -C 4 -alkyl , C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylsulfonyl, amino, C 1 -C 4 -alkylamino, di- (C 1 -C 4 - alkyl) -amino, C 1 -C 4 -alkylcarbonylamino, C 1 -C 4 -alkoxycarbonylamino, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -haloalkoxy-C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl or aminocarbonyl-substituted aryl, heteroaryl, aryl-C 1 -C 4 -alkyl and heteroaryl-C 1 -C 4 -alkyl or NR'R "in which R 'and R" independently of one another represent a radical from the series of hydrogen and C 1 -C 4 alkyl, or
R 8 and R 9
in the radical (C-1) and in the radical (F-1), together with the NS (O) n group to which they are attached, a saturated or unsaturated and optionally halogen, C 1 -C 6 -alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy substituted 5- to 7-membered ring forming one or two heteroatoms selected from sulfur, oxygen (oxygen atoms not immediately adjacent may contain) and nitrogen and / or at least one and preferably exactly one carbonyl group, in particular R 8 and R 9 together with the NS (O) n group to which they are attached, may be a radical from the series
Figure imgb0167
Figure imgb0168
 (in which the arrow in each case marks the bond to the C (X) group),
R 15
for a residue from the series each optionally substituted by methyl C 1 -C 6 alkyl, C 2 -C 6 alkenyl and C 2 -C 6 alkynyl and in each case optionally by methyl, halogen, cyano or Carbamoyl-substituted C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 2 -alkyl and C 3 -C 6 -cycloalkenyl,
R 8 and R 15
in the radical (C-6) together with the NS (O) n group to which they are attached, can form a saturated or unsaturated and optionally substituted 4- to 8-membered ring containing one or two further heteroatoms from the Sulfur, oxygen (oxygen and sulfur atoms may not be immediately adjacent), and nitrogen and / or at least one carbonyl group,
R 17
in each case a halogen radical, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfinyl , C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl and C 1 -C 4 -haloalkylsulfonyl-substituted C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl and C 2 -C 4 -alkynyl, respectively C 3 -C 6 -cycloalkyl optionally substituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 3 -C 6 - Cycloalkyl-C 1 -C 4 -alkyl, C 3 -C 4 -cycloalkenyl, N-pyrrolidinyl, N-piperidinyl, N-morpholinyl, N-thiomorpholinyl, N-thiomorpholinyl-1-oxide, N-thiomorpholinyl-1,1- dioxide, N-piperazinyl, N-1-methylpiperazinyl and N-2-oxo-1-methylpiperazinyl, in each case optionally by halogen, cyano (also in the alkyl part), nitro, C 1 -C 4 -alkyl, C 1 -C 4 - Haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alk ylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylsulfonyl, amino, C 1 -C 4 -alkylamino, di- (C 1 -C 4 -alkyl) -amino, C 1 -C 4 -alkylcarbonylamino, C 1 -C 4 -alkoxycarbonylamino, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -haloalkoxy-C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl or aminocarbonyl-substituted aryl, Heteroaryl, aryl-C 1 -C 4 -alkyl and heteroaryl-C 1 -C 4 -alkyl or NR'R ", wherein R 'and R" independently represent a radical from the series of hydrogen and C 1 -C 4 Alkyl,
R 18
a radical from the series hydrogen, hydroxy, in each case optionally mono- or polysubstituted by halogen or mono- or di-cyano-substituted C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 alkyl, C 1 -C 4 alkyl-SC 1 -C 3 alkyl, C 1 -C 4 alkyl -S (O) -C 1 -C 3 alkyl, C 1 -C 4 alkyl -S (O) 2 -C 1 -C 3 -alkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 - C 3 -alkyl, heterocyclyl, heterocyclyl-C 1 -C 3 -alkyl and in each case optionally mono- to trisubstituted by C 1 -C 4 -alkyl, C 1 -C 3 -haloalkyl, C 1 -C 3 -alkoxy, C 1 - C 3 haloalkoxy, cyclopropyl, fluorine is chlorine, bromine or cyano-substituted phenyl, benzyl, pyridyl, pyrimidyl, thiazolyl, oxazolyl, pyrazolyl, thienyl, furanyl, pyridinylmethyl and thiazolylmethyl,
R 19
is hydrogen, an alkali or alkaline earth metal ion, an optionally monosubstituted to fourfold C 1 -C 4 alkyl substituted ammonium ion, or each optionally optionally simple or C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl or C 1 -C 4 -alkyl which is monosubstituted by halogen or mono- or disubstituted by cyano and C 1 - C 4 alkyl-SC 1 -C 2 -alkyl, C 1 -C 4 -alkyl-S (O) -C 1 -C 2 -alkyl and C 1 -C 4 -alkyl-S (O) 2 -C 1 C 2 alkyl,
Y 3
a radical selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 haloalkoxy,
W
is a radical from the series S, SO and SO 2 ,
R 22
a radical selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, C 2 -C 4 -haloalkyl, cyano-C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, optionally C 1 -C 2 -alkoxy-C 1 -C 4 -substituted by halogen alkyl, optionally halogen-substituted bis (C 1 -C 2 -alkoxy) C 1 -C 4 -alkyl, optionally halogen-substituted C 1 -C 4 -alkylsulfanyl-C 1 -C 4 -alkyl, optionally halogen-substituted C C 1 -C 4 -alkylcarbonyl-C 1 -C 4 -alkyl, optionally halogen-substituted C 1 -C 4 -alkylsulfinyl-C 1 -C 4 -alkyl, optionally C 1 -C 4 -alkylsulfonyl-C 1 substituted by halogen - C 4 alkyl, di- (C 1 -C 4 alkyl) -aminosulfanyl-C 1 -C 4 alkyl, di- (C 1 -C 4 alkyl) -aminosulfinyl-C 1 -C 4 alkyl, di - (C 1 -C 4 alkyl) -aminosulfonyl-C 1 -C 4 alkyl, optionally substituted by halogen C 1 -C 4 alkoxycarbonyl, optionally substituted by halogen subs substituted C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl, optionally halogen-substituted C 2 -C 4 -alkynyloxy, optionally halogen-substituted C 2 -C 4 -alkoxyloxycarbonyl, di (C 1 -C 4 -) alkyl) -aminocarbonyl, NC 1 -C 4 -alkyl-NC 3 -C 6 -cycloalkylaminocarbonyl, di- (C 1 -C 4 -alkyl) -aminocarbonyl-C 1 -C 4 -alkyl, NC 1 -C 4 -alkyl -NC 3 -C 6 -cycloalkylaminocarbonyl-C 1 -C 4 -alkyl, heterocyclylcarbonyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkylsulfanyl, C 1 -C 4 -haloalkylsulfanyl, C 1 -C 4 -alkylsulfinyl , C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylsulfonyl, optionally substituted by halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -haloalkoxycarbonyl or pyridyl (which may itself be represented by C 1 -C 4 Substituted alkyl or halogen) substituted C 3 -C 6 -cycloalkyl, optionally substituted by halogen, cyano, nitro, C C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkoxycarbonyl, C 1 - C 4 -haloalkoxycarbonyl or pyridyl (which is optionally itself substituted by C 1 -C 4 -alkyl or halogen) substituted C 3 -C 6 -cycloalkylcarbonyl, optionally substituted by halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -haloalkoxycarbonyl, pyridyl, pyrimidyl, Pyrazanyl, pyridazinyl, thiazolyl, isothiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, pyrazolyl, triazinyl or triazolyl (where the said hetaryl are unsubstituted or themselves substituted by C 1 -C 4 -alkyl or halogen) substituted C 3 -C 6 -cycloalkyl- C 1 -C 4 -alkyl, where appropriate by halogen, cyano (also in the C 1 -C 4 -alkyl portion of heterocyclyl-C 1 -C 4 -alkyl), nitro, hydroxy, C 1 -C 4 -alkyl, C 1 - C 4 haloalkyl, C 3 -C 6 cycloal kyl (which is optionally substituted by halogen, cyano, C 1 -C 4 alkyl and C 3 -C 6 -cycloalkyl is substituted), C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 - Alkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -haloalkylsulfonyl, amino, C 1 -C 4 -alkylamino, di- (C 1 -C 4 -alkyl) -amino, C 1 -C 4 -alkylcarbonylamino, C 1 -C 4 -alkoxycarbonylamino, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -haloalkoxy-C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl or aminocarbonyl-substituted heterocyclyl- C 1 -C 4 -alkyl, optionally substituted by halogen, cyano, nitro, hydroxy, amino, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl (which is optionally substituted by halogen, cyano C 1 -C 4 -alkyl and C 3 -C 6 -cycloalkyl), C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy-substituted aryl, optionally substituted by halogen, cyano (also in the C 1 -C 4- alkyl moiety of Ary 1-C 1 -C 4 -alkyl), nitro, hydroxy, amino, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl (which is optionally substituted by halogen, cyano, C 1 -C 4- alkyl and C 3 -C 6 -cycloalkyl), C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy-substituted aryl-C 1 -C 4 -alkyl, optionally substituted by halogen, cyano (also in the C C 1 -C 4 -alkyl portion of hetaryl-C 1 -C 4 -alkyl), nitro, hydroxy, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl (which may be replaced by halogen , Cyano, C 1 -C 4 -alkyl and C 3 -C 6 -cycloalkyl), C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 haloalkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, amino, C 1 -C 4 alkylamino, di- (C 1 -C 4 alkyl) amino, C 1 -C 4 alkylcarbonylamino, C 1 -C 4 alkoxycarbonylamino, C 1 -C 4 -alkoxy-C 1 -C 4 alkyl, C 1 -C 4 haloalkoxy C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 Alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl or aminocarbonyl-substituted hetaryl-C 1 -C 4 -alkyl, or
R 22
for a D radical from the series (D-1) to (D-3)
Figure imgb0169
 or for one of the following E radicals
Figure imgb0170
Figure imgb0171
Figure imgb0172
Figure imgb0173
Figure imgb0174
 stands, or, in the case R 2 = d),
R 22
also for the rest (E-13)
Figure imgb0175
 stands,
R 23
a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 1 -C 6 alkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy, C 3 -C 6 cycloalkyloxy, C 1 -C 4 alkylthio-C 1 -C 4 alkyl, C 2 -C 4- alkenylthio-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl,
or, for R 2 = c) or g),
R 22 and R 23
together with the nitrogen atom to which they are attached form a saturated four- to six-membered ring which may contain another nitrogen, oxygen and sulfur heteroatoms,
R 26
a radical selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl, C 1 -C 4 -alkylsulfanyl, C 1 -C 4 -haloalkylsulfanyl, C 1 -C 4- alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -alkylthio-C 1 -C 2 -alkyl, C 1 -C 4 -alkylsulfinyl-C 1 -C 2 - alkyl, C 1 -C 4 -alkylsulfonyl-C 1 -C 2 -alkyl and cyano-C 1 -C 4 -alkyl and
R 27
is hydrogen, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl , C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 2 -alkyl, C 1 -C 4 -alkylsulfinyl-C 1 -C 2 -alkyl, C C 1 -C 4 -alkylsulfonyl-C 1 -C 2 -alkyl or cyano-C 1 -C 4 -alkyl and
Compounds of formula (I) wherein
A
for the A-rest
Figure imgb0176
 in which the dashed line denotes the bond to the carbon atom of the bicyclic compound of the formula (I),
G 1
stands for N or CB 1 ,
B 1
a radical selected from the group consisting of hydrogen, halogen, C 1 -C 6 -alkyl and C 1 -C 4 -haloalkyl,
B 2
a radical selected from the group consisting of hydrogen, halogen, C 1 -C 6 -alkyl and C 1 -C 4 -haloalkyl,
T
stands for oxygen or a pair of electrons,
Q
stands for sulfur,
R 1
a radical selected from the group consisting of hydrogen, C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy,
R 2
a) for a B residue from the series
Figure imgb0177
Figure imgb0178
Figure imgb0179
Figure imgb0180
Figure imgb0181
Figure imgb0182
Figure imgb0183
 wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R 2
c) a radical of the formula
Figure imgb0184
 wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R 2
d) for a radical of the formula
Figure imgb0185
 wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R 2
e) for an F radical from the series (F-8) and (F-10)
Figure imgb0186
 wherein the dashed line represents the bond to the carbon atom in the formula (I), or
R 2
f) is a radical from the series C 1 -C 6 -haloalkyl and carboxyl,
R 2
g) for a radical of the formula
Figure imgb0187
 wherein the dotted line represents the bond to the carbon atom of the bicyclic moiety of formula (I) wherein
G 2
is hydrogen or a radical selected from halogen, nitro, amino, cyano, C 1 -C 4 -alkylamino, halo-C 1 -C 4 -alkylamino, di- (C 1 -C 4 -alkyl) -amino, C 1 C 4 alkyl, halo C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halo C 1 -C 4 alkoxy, C 1 -C 4 alkoxy-C 1 -C 4 alkyl, halogenated C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, bis (C 1 -C 4 -alkoxy) C 1 -C 4 -alkyl, bis (halogeno-C 1 -C 4 -alkoxy) -C C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy- (C 1 -C 4 -alkylsulfanyl) C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy- (C 1 -C 4 -alkylsulfinyl) C 1 -C 4 alkyl, C 1 -C 4 alkoxy (C 1 -C 4 alkylsulfonyl) C 1 -C 4 alkyl, bis (C 1 -C 4 alkylsulfanyl) C 1 -C 4- alkyl, bis (halo-C 1 -C 4 alkylsulfanyl) C 1 -C 4 alkyl, bis (hydroxy C 1 -C 4 alkylsulfanyl) C 1 -C 4 alkyl, C 1 -C 4- alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl, C (X 2 ) NR 3 R 4 , NR 6 R 7 , C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfinyl , C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -haloalkylsulfo nyl, the heterocyclyl dioxanyl, dioxolanyl, dioxepanyl, Dioxocanyl, Oxathianyl, Oxathiolanyl, Oxathiepanyl, Oxathiocanyl, dithianyl, dithiolanyl, Dithiepanyl, Dithiocanyl, Oxathianyloxid, Oxathiolanyloxid, Oxathiepanyloxid, Oxathiocanyloxid, Oxathianyldioxid, Oxathiolanyldioxid, Oxathiepanyldioxid, Oxathiocanyldioxid, morpholinyl, Triazolinonyl, oxazolinyl, Dihydrooxadiazinyl, dihydrodioxazinyl, dihydrooxazolyl, dihydrooxazinyl and pyrazolinonyl (which in turn may be substituted by C 1 -C 4 alkyl, halo-C 1 -C 4 alkyl, C 1 -C 4 alkoxy and C 1 -C 4 alkoxy C 1 -C 4 -alkyl), phenyl (which in turn may itself be substituted by halogen, cyano, nitro, C 1 -C 4 -alkyl and halogeno-C 1 -C 4 -alkyl), the heteroaryl radicals pyridyl, pyridyl- N- oxide, pyrimidyl, imidazolyl, pyrazolyl, oxazolyl, thiazolyl, furanyl, thienyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyrazinyl, triazinyl, tetrazinyl and isoquinolinyl (which itself is substituted again n can be substituted by halogen, nitro, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halogeno-C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl and C 3 -C 6 -cycloalkyl) and the heteroaryl-C 1 -C 4 alkyl radicals triazolyl-C 1 -C 4 -alkyl, pyridyl-C 1 -C 4 -alkyl, pyrimidyl-C 1 -C 4 -alkyl and oxadiazolyl-C 1 -C 4 -alkyl (which in turn may be substituted by halogen and C 1 -C 4 -alkyl), or
G 2
for a C-residue from the series (C-1), (C-6) and (C-9)
Figure imgb0188
 wherein the dashed line indicates the bond to the B radicals,
X
stands for oxygen,
X 2
is oxygen, sulfur, NR 5 or NOH,
n
stands for 2,
R 3
is C 1 -C 4 -alkyl,
R 4
a radical selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 2 -C 4 -alkynyl, C 3 -C 6 - Cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl- C 1 -C 4 -alkyl and C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl,
R 5
a radical selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 2 -C 4 -alkynyl, C 3 -C 6 - Cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl- C 1 -C 4 -alkyl and C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl,
R 6
is hydrogen or C 1 -C 4 -alkyl,
R 7
a radical selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 2 -C 4 -alkynyl, C 1 -C 4 - Alkoxy, halo-C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 - alkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, aryl-C 1 -C 4 -alkyl or hetaryl-C 1 -C 4 -alkyl, or
R 6 and R 7
together with the nitrogen atom to which they are attached form a 4- to 7-membered ring which may contain one or two further nitrogen, oxygen and sulfur heteroatoms (oxygen and sulfur atoms not being immediately adjacent);
R 8
a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, cyano-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, in each case optionally halogen-substituted C 1 -C 6 -alkylcarbonyl and C 1 -C 6 -alkylsulfonyl, optionally C-substituted by halogen C 1 -C 6 -alkoxycarbonyl and optionally substituted by halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkyl and cyano-substituted C 3 -C 6 -cycloalkylcarbonyl, or a cation or an ammonium ion which is optionally substituted by C 1 -C 6 -alkyl or aryl-C 1 -C 6 -alkyl,
R 9
in each case a halogen radical, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfinyl , C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl and C 1 -C 4 -haloalkylsulfonyl-substituted C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl and C 2 -C 4 -alkynyl, respectively C 3 -C 6 -cycloalkyl optionally substituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 3 -C 6 - Cycloalkyl-C 1 -C 4 -alkyl and C 3 -C 4 -cycloalkenyl in which one or two ring members in each case by a heteroatom selected from the group sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen may be replaced (and especially for
Figure imgb0189
 wherein the arrow in each case marks the bond to the S atom in the radical (C-1)), in each case optionally by halogen, cyano (also in the alkyl part), nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl , C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, amino, C 1 -C 4 alkylamino, di- (C 1 -C 4 alkyl) amino, C 1 - C 4 -alkylcarbonylamino, C 1 -C 4 -alkoxycarbonylamino, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -haloalkoxy-C 1 -C 4 -alkyl, C 2 -C 4 Alkenyl, C 2 -C 4 alkynyl, C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl, C 1 -C 4 alkylcarbonyl, C 1 -C 4 alkoxycarbonyl or aminocarbonyl-substituted aryl, heteroaryl, aryl C 1 -C 4 alkyl and heteroaryl-C 1 -C 4 alkyl or NR'R ", wherein R 'and R" independently represent a radical from the series of hydrogen and C 1 -C 4 alkyl , or
R 8 and R 9
in the radical (C-1) also together with the NS (O) n group to which they are attached, a saturated or unsaturated and optionally halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy substituted 5- to 7-membered ring forming one or two heteroatoms selected from sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen and / or at least one and preferably can contain exactly one carbonyl group, in particular R 8 and R 9 can together with the NS (O) n group to which they are attached, for a residue from the series
Figure imgb0190
Figure imgb0191
 (in which the arrow in each case marks the bond to the C (X) group),
R 15
C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl and C 2 -C 6 -alkynyl, each of which is optionally substituted by methyl, and C 3 -C, in each case optionally substituted by methyl, halogen, cyano or carbamoyl, 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 2 -alkyl and C 3 -C 6 -cycloalkenyl,
R 8 and R 15
in the radical (C-6) together with the NS (O) n group to which they are attached, can form a saturated or unsaturated and optionally substituted 4- to 8-membered ring containing one or two further heteroatoms from the Sulfur, oxygen (oxygen and sulfur atoms may not be immediately adjacent), and nitrogen and / or at least one carbonyl group,
R 17
in each case a halogen radical, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfinyl , C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl and C 1 -C 4 -haloalkylsulfonyl-substituted C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl and C 2 -C 4 -alkynyl, respectively C 3 -C 6 -cycloalkyl optionally substituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 3 -C 6 - Cycloalkyl-C 1 -C 4 -alkyl, C 3 -C 4 -cycloalkenyl, N-pyrrolidinyl, N-piperidinyl, N-morpholinyl, N-thiomorpholinyl, N-thiomorpholinyl-1-oxide, N-thiomorpholinyl-1,1- dioxide, N-piperazinyl, N-1-methylpiperazinyl and N-2-oxo-1-methylpiperazinyl, in each case optionally by halogen, cyano (also in the alkyl part), nitro, C 1 -C 4 -alkyl, C 1 -C 4 - Haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alk ylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylsulfonyl, amino, C 1 -C 4 -alkylamino, di- (C 1 -C 4 -alkyl) -amino, C 1 -C 4 -alkylcarbonylamino, C 1 -C 4 -alkoxycarbonylamino, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -haloalkoxy-C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl or aminocarbonyl-substituted aryl, Heteroaryl, aryl-C 1 -C 4 -alkyl and heteroaryl-C 1 -C 4 -alkyl or NR'R ", wherein R 'and R" independently represent a radical from the series of hydrogen and C 1 -C 4 Alkyl, and in the case where R 2 is g),
R 22
a radical selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, C 2 -C 4 -haloalkyl, cyano-C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, optionally C 1 -C 2 -alkoxy-C 1 -C 4 -substituted by halogen alkyl, optionally halogen-substituted bis (C 1 -C 2 -alkoxy) C 1 -C 4 -alkyl, optionally halogen-substituted C 1 -C 4 -alkylsulfanyl-C 1 -C 4 -alkyl, optionally halogen-substituted C C 1 -C 4 -alkylcarbonyl-C 1 -C 4 -alkyl, optionally halogen-substituted C 1 -C 4 -alkylsulfinyl-C 1 -C 4 -alkyl, optionally C 1 -C 4 -alkylsulfonyl-C 1 substituted by halogen - C 4 alkyl, di- (C 1 -C 4 alkyl) -aminosulfanyl-C 1 -C 4 alkyl, di- (C 1 -C 4 alkyl) -aminosulfinyl-C 1 -C 4 alkyl, di - (C 1 -C 4 alkyl) -aminosulfonyl-C 1 -C 4 alkyl, optionally substituted by halogen C 1 -C 4 alkoxycarbonyl, optionally substituted by halogen subs substituted C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl, optionally halogen-substituted C 2 -C 4 -alkynyloxy, optionally halogen-substituted C 2 -C 4 -alkoxyloxycarbonyl, di (C 1 -C 4 -) alkyl) -aminocarbonyl, NC 1 -C 4 -alkyl-NC 3 -C 6 -cycloalkylaminocarbonyl, di- (C 1 -C 4 -alkyl) -aminocarbonyl-C 1 -C 4 -alkyl, NC 1 -C 4 -alkyl -NC 3 -C 6 -cycloalkylaminocarbonyl-C 1 -C 4 -alkyl, heterocyclylcarbonyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkylsulfanyl, C 1 -C 4 -haloalkylsulfanyl, C 1 -C 4 -alkylsulfinyl , C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylsulfonyl, optionally substituted by halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -haloalkoxycarbonyl or pyridyl (which may itself be represented by C 1 -C 4 Substituted alkyl or halogen) substituted C 3 -C 6 -cycloalkyl, optionally substituted by halogen, cyano, nitro, C C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkoxycarbonyl, C 1 - C 4 -haloalkoxycarbonyl or pyridyl (which is optionally itself substituted by C 1 -C 4 -alkyl or halogen) substituted C 3 -C 6 -cycloalkylcarbonyl, optionally substituted by halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -haloalkoxycarbonyl, pyridyl, pyrimidyl, Pyrazanyl, pyridazinyl, thiazolyl, isothiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, pyrazolyl, triazinyl or triazolyl (where the said hetaryl are unsubstituted or themselves substituted by C 1 -C 4 -alkyl or halogen) substituted C 3 -C 6 -cycloalkyl- C 1 -C 4 -alkyl, where appropriate by halogen, cyano (also in the C 1 -C 4 -alkyl portion of heterocyclyl-C 1 -C 4 -alkyl), nitro, hydroxy, C 1 -C 4 -alkyl, C 1 - C 4 haloalkyl, C 3 -C 6 cycloal kyl (which is optionally substituted by halogen, cyano, C 1 -C 4 -alkyl and C 3 -C 6 -cycloalkyl), C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 - alkylthio, C 1 -C 4 haloalkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, amino, C 1 -C 4 - Alkylamino, di- (C 1 -C 4 -alkyl) amino, C 1 -C 4 -alkylcarbonylamino, C 1 -C 4 -alkoxycarbonylamino, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 haloalkoxy-C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4- alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl or aminocarbonyl-substituted heterocyclyl-C 1 -C 4 -alkyl, optionally substituted by halogen, cyano, nitro, hydroxy, amino, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl (which is optionally substituted by halogen, cyano, C 1 -C 4 -alkyl and C 3 -C 6 -cycloalkyl is substituted), C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy-substituted aryl, optionally substituted by halogen, cyano (also in the C 1 -C 4 -alkyl portion of aryl-C 1 C 4 -C 4 alkyl), nitro, hydroxy, amino, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl (which is optionally substituted by halogen, cyano, C 1 -C 4 - Alkyl and C 3 -C 6 -cycloalkyl), C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy-substituted aryl-C 1 -C 4 -alkyl, where appropriate by halogen, cyano (also in the C 1 - C 4 alkyl portion of hetaryl C 1 -C 4 alkyl), nitro, hydroxy, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl (which is optionally substituted by halogen, cyano , C 1 -C 4 -alkyl and C 3 -C 6 -cycloalkyl), C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylth io, C 1 -C 4 haloalkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, amino, C 1 -C 4 - Alkylamino, di- (C 1 -C 4 -alkyl) amino, C 1 -C 4 -alkylcarbonylamino, C 1 -C 4 -alkoxycarbonylamino, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 haloalkoxy-C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4- alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl or aminocarbonyl-substituted hetaryl-C 1 -C 4 -alkyl, and in the case where R 2 is g),
R 22
for a D radical from the series (D-1) to (D-3)
Figure imgb0192
 wherein
X 1
a radical selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 - Alkoxy and C 1 -C 4 -haloalkoxy,
R
for NR 18 R 19 or for any monosubstituted to trisubstituted by halogen, monosubstituted or disubstituted by oxygen (leads to C = O) or mono- or disubstituted by cyano-substituted C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 1 -C 4 -alkoxy-C 1 -C 3 -alkyl, C 1 -C 4 -alkyl-SC 1 -C 3 -alkyl, C 1 -C 4 -alkyl-S ( O) -C 1 -C 3 -alkyl, C 1 -C 4 -alkyl-S (O) 2 -C 1 -C 3 -alkyl, for R 18 -CO-C 1 -C 2 -alkyl, for NR 18 R 19 -CO-C 1 -C 2 -alkyl, optionally optionally mono- or disubstituted by oxygen (leads to C = O), C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 - Alkoxy and C 1 -C 4 -haloalkyl substituted C 3 -C 6 -cycloalkyl, optionally substituted once or twice by oxygen (leads to C = O), C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkyl-substituted C 3 -C 8 -cycloalkenyl, optionally substituted once or twice by oxygen (leads to C = O), C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkyl-substituted C 3 - C 6 -Cycloalkyl-C 1 -C 4 -alkyl, optionally optionally mono- or disubstituted by oxygen (leads to C = O), C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 - Alkoxy and C 1 -C 4 -haloalkyl-substituted C 3 -C 6 -cycloalkenyl-C 1 -C 4 -alkyl, optionally substituted once or twice by oxygen (leads to C = O), C 1 -C 4 -alkyl, C C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkyl-substituted heterocyclyl, optionally substituted once or twice by oxygen (leads to C = O), C 1 -C 4 -alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy and C 1 -C 4 -halogenoalkyl-substituted heterocyclyl-Ci-C4-alkyl or represents in each case optionally mono- to trisubstituted by halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy substituted phenyl, phenyl-C 1 -C 4 -alkyl, hetaryl and hetaryl-C 1 -C 4 -alkyl,
Y 3
a radical selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 haloalkoxy,
W
is a radical from the series S, SO and SO 2 ,
R 22
furthermore for one of the following E radicals
Figure imgb0193
Figure imgb0194
Figure imgb0195
Figure imgb0196
Figure imgb0197
 stands, or, in the case R 2 = d),
R 22
also for the rest (E-13)
Figure imgb0198
 stands,
R 18
a radical from the series hydrogen, hydroxy, in each case optionally mono- or polysubstituted by halogen or mono- or di-cyano-substituted C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 alkyl, C 1 -C 4 alkyl-SC 1 -C 3 alkyl, C 1 -C 4 alkyl -S (O) -C 1 -C 3 alkyl, C 1 -C 4 alkyl -S (O) 2 -C 1 -C 3 -alkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 - C 3 -alkyl, heterocyclyl, heterocyclyl-C 1 -C 3 -alkyl and in each case optionally mono- to trisubstituted by C 1 -C 4 -alkyl, C 1 -C 3 -haloalkyl, C 1 -C 3 -alkoxy, C 1 - C 3 haloalkoxy, cyclopropyl, fluorine is chlorine, bromine or cyano-substituted phenyl, benzyl, pyridyl, pyrimidyl, thiazolyl, oxazolyl, pyrazolyl, thienyl, furanyl, pyridinylmethyl and thiazolylmethyl,
R 19
for hydrogen, for an alkali or alkaline earth metal ion, for an optionally monosubstituted to monosubstituted by C 1 -C 4 -alkyl-substituted ammonium ion or for a particular monosubstituted or polysubstituted by halogen or mono- or disubstituted cyano-substituted radical from the series C 1 - C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkoxy-C 1 -C 2 alkyl, C 1 -C 4 alkyl-SC 1 -C 2 alkyl, C 1 -C 4 -Alkyl-S (O) -C 1 -C 2 -alkyl and C 1 -C 4 -alkyl-S (O) 2 -C 1 -C 2 -alkyl,
R 23
a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 1 -C 6 alkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy, C 3 -C 6 cycloalkyloxy, C 1 -C 4 alkylthio-C 1 -C 4 alkyl, C 2 -C 4- alkenylthio-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl,
or, for R 2 = g),
R 22 and R 23
together with the nitrogen atom to which they are attached form a saturated four- to six-membered ring which may contain another nitrogen, oxygen and sulfur heteroatoms,
R 26
a radical selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl, C 1 -C 4 -alkylsulfanyl, C 1 -C 4 -haloalkylsulfanyl, C 1 -C 4- alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -alkylthio-C 1 -C 2 -alkyl, C 1 -C 4 -alkylsulfinyl-C 1 -C 2 - alkyl, C 1 -C 4 -alkylsulfonyl-C 1 -C 2 -alkyl and cyano-C 1 -C 4 -alkyl and
R 27
is hydrogen, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl , C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 2 -alkyl, C 1 -C 4 -alkylsulfinyl-C 1 -C 2 -alkyl, C C 1 -C 4 -alkylsulfonyl-C 1 -C 2 -alkyl or cyano-C 1 -C 4 -alkyl.

Vorzugsbereich (3): Ganz besonders bevorzugt sind Verbindungen der Formel (I), in welchen

A
für einen A-Rest aus der Reihe (A-b) und (A-f)
Figure imgb0199
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet,
B2
für Wasserstoff steht,
Q
für Schwefel setht,
R1
für Wasserstoff steht,
R2
für einen B-Rest aus der Reihe
Figure imgb0200
Figure imgb0201
Figure imgb0202
Figure imgb0203
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder
R2
b) für einen D-Rest aus der Reihe (D-1) bis (D-3)
Figure imgb0204
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder
R2
c) für einen Rest der Formel
Figure imgb0205
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder
R2
d) für einen Rest der Formel
Figure imgb0206
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder
R2
e) für einen F-Rest aus der Reihe (F-1), (F-8) und (F-10)
Figure imgb0207
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder
R2
f) für einen Rest aus der Reihe C1-C6-Halogenalkyl und Carboxyl steht, oder
R2
g) für einen Rest der Formel
Figure imgb0208
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, worin
G2
für Wasserstoff oder einen Rest aus der Reihe Halogen, Nitro, Amino, Cyano, C1-C4-Alkylamino, Halogen C1-C4-Alkylamino, Di-(C1-C4-alkyl)-amino, C1-C4-Alkyl, Halogen-C1-C4-alkyl, C1-C4-Alkoxy, Halogen-C1-C4-alkoxy, C1-C4-Alkoxy-C1-C4-alkyl, halogeniertes C1-C4-Alkoxy-C1-C4-alkyl, Bis(C1-C4-alkoxy)-C1-C4-alkyl, Bis(halogen-C1-C4-alkoxy)-C1-C4-alkyl, C1-C4-Alkoxy(C1-C4-alkylsulfanyl)-C1-C4-alkyl, C1-C4-Alkoxy(C1-C4-alkylsulfinyl)-C1-C4-alkyl, C1-C4-Alkoxy(C1-C4-alkylsulfonyl)-C1-C4-alkyl, Bis(C1-C4-alkylsulfanyl)-C1-C4-alkyl, Bis(halogen-C1-C4-alkylsulfanyl)-C1-C4-alkyl, Bis(hydroxy-C1-C4-alkylsulfanyl)-C1-C4-alkyl, C1-C4-Alkoxycarbonyl, C1-C4-Alkoxycarbonyl-C1-C4-alkyl, C(X2)NR3R4, NR6R7, C1-C4-Alkylthio, C1-C4-Alkylsulfinyl, C1-C4-Alkylsulfonyl, C1-C4-Halogenalkylthio, C1-C4-Halogenalkylsulfinyl und C1-C4-Halogenalkylsulfonyl steht, oder
G2
für einen C-Rest (C-1) oder (C-9)
Figure imgb0209
 steht, worin die gestrichelte Linie die Bindung zu den B-Resten bedeutet,
X
für Sauerstoff steht,
X1
für einen Rest aus der Reihe Wasserstoff, Fluor, Chlor, Brom, Cyano, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy, Difluormethoxy und Trifluormethoxy steht,
X2
für Sauerstoff, Schwefel, NR5 oder NOH steht,
n
für 2 steht,
R
für NR18R19 oder für einen jeweils gegebenfalls einfach, zweifach, dreifach, vierfach oder fünffach durch Fluor, Chlor oder einfach oder zweifach durch Cyano substituierten Rest aus der Reihe C1-C4-Alkyl, C3-C4-Alkenyl, C3-C4-Alkinyl, C1-C2-Alkoxy-C1-C2-alkyl und C1-C2-Alkyl-S-C1-C2-alkyl, C1-C2-Alkyl-S(O)-C1-C2-alkyl, C1-C2-Alkyl-S(O)2-C1-C2-alkyl, für R18-CO-C1-C2-alkyl, für NR18R19-CO-C1-C2-alkyl, für gegebenenfalls einfach oder zweifach durch C1-C2-Alkyl, C1-C2-Alkoxy oder C1-C2-Halogenalkyl oder durch ein Sauerstoffatom (führt zu C=O) substituiertes C3-C6-Cycloalkyl, für gegebenenfalls einfach oder zweifach durch C1-C2-Alkyl, C1-C2-Alkoxy oder C1-C2-Halogenalkyl oder durch ein Sauerstoffatom (führt zu C=O) substituiertes C3-C6-Cycloalkenyl, für gegebenenfalls einfach bis zweifach durch C1-C2-Alkyl, C1-C2-Alkoxy oder C1-C2-Halogenalkyl substituiertes C3-C6-Cycloalkyl-C1-C2-alkyl, für gegebenenfalls einfach oder zweifach durch C1-C2-Alkyl, C1-C2-Alkoxy oder C1-C2-Halogenalkyl substituiertes C3-C6-Cycloalkenyl-C1-C2-alkyl, für gegebenenfalls einfach oder zweifach durch C1-C2-Alkyl, C1-C2-Alkoxy oder C1-C2-Halogenalkyl substituiertes Heterocyclyl, für gegebenenfalls einfach oder zweifach durch C1-C2-Alkyl, C1-C2-Alkoxy oder C1-C2-Halogenalkyl substituiertes Heterocyclyl-C1-C2-alkyl oder für jeweils gegebenenfalls einfach oder zweifach durch Fluor, Chlor, Brom, Cyano, Methyl, Ethyl, Difluormethyl, Trifluormethyl, Methoxy, Ethoxy, Difluormethoxy oder Trifluormethoxy substituiertes Phenyl, Benzyl, Pyridyl, Pyrimidyl, Thiazolyl, Oxazolyl, Pyrazolyl, Thienyl, Furanyl, Pyridinylmethyl oder Thiazolylmethyl steht,
R3
für C1-C4-Alkyl steht,
R4
für einen Rest aus der Reihe Wasserstoff, C1-C4-Alkyl, Halogen-C1-C4-alkyl, Cyano-C1-C4-alkyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C4-alkyl, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4-Alkoxycarbonyl, C1-C4-Alkoxycarbonyl-C1-C4-alkyl und C1-C4-Alkylthio-C1-C4-alkyl steht,
R5
für einen Rest aus der Reihe Wasserstoff, C1-C4-Alkyl, Halogen-C1-C4-alkyl, Cyano-C1-C4-alkyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C4-alkyl, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4-Alkoxycarbonyl, C1-C4-Alkoxycarbonyl-C1-C4-alkyl und C1-C4-Alkylthio-C1-C4-alkyl steht,
R6
für Wasserstoff oder C1-C4-Alkyl steht,
R7
für einen Rest aus der Reihe Wasserstoff, C1-C4-Alkyl, Halogen-C1-C4-alkyl, Cyano-C1-C4-alkyl, C2-C4-Alkinyl, C1-C4-Alkoxy, Halogen-C1-C4-alkoxy, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4-Alkoxycarbonyl, C1-C4-Alkoxycarbonyl-C1-C4-alkyl, C1-C4-Alkylthio-C1-C4-alkyl, Aryl-C1-C4-alkyl oder Hetaryl-C1-C4-alkyl steht oder
R6 und R7
gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen 4- bis 7-gliedrigen Ring bilden, der ein oder zwei weitere Heteroatome aus der Reihe Stickstoff, Sauerstoff und Schwefel (wobei Sauerstoff- und Schwefelatome nicht unmittelbar benachbart sein dürfen) enthalten kann,
R8
für einen Rest aus der Reihe Wasserstoff, C1-C6-Alkyl, C1-C6-Halogenalkyl, Cyano-C1-C6-alkyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C2-C6-Alkenyl, C1-C6-Alkoxy-C1-C6-alkyl, jeweils gegebenenfalls durch Halogen substituiertes C1-C6-Alkylcarbonyl und C1-C6-Alkylsulfonyl, gegebenenfalls durch Halogen substituiertes C1-C6-Alkoxycarbonyl, gegebenenfalls durch Halogen, C1-C6-Alkyl, C1-C6-Alkoxy, C1-C6-Halogenalkyl und Cyano substituiertes C3-C6-Cycloalkylcarbonyl, oder für ein Kation oder ein gegebenenfalls durch C1-C6-Alkyl oder Aryl-Ci-C6-alkyl substituiertes Ammonium-Ion steht,
R9
für einen Rest aus der Reihe jeweils gegebenenfalls durch Halogen, C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C1-C4-Alkylthio, C1-C4-Halogenalkylthio, C1-C4-Alkylsulfinyl, C1-C4-Halogenalkylsulfinyl, C1-C4-Alkylsulfonyl und C1-C4-Halogenalkylsulfonyl substituiertes C1-C4-Alkyl, C2-C4-Alkenyl und C2-C4-Alkinyl, jeweils gegebenenfalls durch Halogen, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy substituiertes C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C4-alkyl und C3-C4-Cycloalkenyl, in welchen ein oder zwei Ringglieder jeweils durch ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff ersetzt sein können (und dabei insbesondere für
Figure imgb0210
 wobei der Pfeil jeweils die Bindung zum S-Atom im Rest (C-1) und im Rest (F-1) markiert), jeweils gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, C1-C4-Alkyl, C1-C4-Halogenalkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C1-C4-Alkylthio, C1-C4-Halogenalkylthio, C1-C4-Alkylsulfinyl, C1-C4-Halogenalkylsulfinyl, C1-C4-Alkylsulfonyl, C1-C4-Halogenalkylsulfonyl, Amino, C1-C4-Alkylamino, Di-(C1-C4-alkyl)-amino, C1-C4-Alkylcarbonylamino, C1-C4-Alkoxycarbonylamino, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4-Halogenalkoxy-C1-C4-alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl-C1-C4-alkyl, C1-C4-Alkylcarbonyl, C1-C4-Alkoxycarbonyl oder Aminocarbonyl substituiertes Aryl, Heteroaryl, Aryl-C1-C4-alkyl und Heteroaryl-C1-C4-alkyl oder für NR'R" steht, worin R' und R" unabhängig voneinander für einen Rest aus der Reihe Wasserstoff und C1-C4-Alkyl stehen,
R8 und R9
können im Rest (C-1) und im Rest (F-1) auch zusammen mit der N-S(O)n Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls durch Halogen, C1-C6-Alkyl, C1-C6-Halogenalkyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy substituierten 5- bis 7-gliedrigen Ring bilden, der ein oder zwei Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine und bevorzugt eine Carbonylgruppe enthalten kann, insbesondere können R8 und R9 zusammen mit der N-S(O)n Gruppe, an die sie gebunden sind, für einen Rest aus der Reihe
Figure imgb0211
Figure imgb0212
 stehen (worin der Pfeil jeweils die Bindung zur C(X)-Gruppe markiert),
R17
für einen Rest aus der Reihe jeweils gegebenenfalls durch Halogen, C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C1-C4-Alkylthio, C1-C4-Halogenalkylthio, C1-C4-Alkylsulfinyl, C1-C4-Halogenalkylsulfinyl, C1-C4-Alkylsulfonyl und C1-C4-Halogenalkylsulfonyl substituiertes C1-C4-Alkyl, C2-C4-Alkenyl und C2-C4-Alkinyl, jeweils gegebenenfalls durch Halogen, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy substituiertes C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C4-alkyl und C3-C4-Cycloalkenyl, N-Pyrrolidinyl, N-Piperidinyl, N-Morpholinyl, N-Thiomorpholinyl, N-Thiomorpholinyl-1-oxid, N-Thiomorpholinyl-1,1-dioxid, N-Piperazinyl, N-1-Methylpiperazinyl oder N-2-Oxo-1-methylpiperazinyl, jeweils gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, C1-C4-Alkyl, C1-C4-Halogenalkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C1-C4-Alkylthio, C1-C4-Halogenalkylthio, C1-C4-Alkylsulfinyl, C1-C4-Halogenalkylsulfinyl, C1-C4-Alkylsulfonyl, C1-C4-Halogenalkylsulfonyl, Amino, C1-C4-Alkylamino, Di-(C1-C4-alkyl)-amino, C1-C4-Alkylcarbonylamino, C1-C4-Alkoxycarbonylamino, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4-Halogenalkoxy-C1-C4-alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl-C1-C4-alkyl, C1-C4-Alkylcarbonyl, C1-C4-Alkoxycarbonyl oder Aminocarbonyl substituiertes Aryl, Heteroaryl, Aryl-C1-C4-alkyl und Heteroaryl-C1-C4-alkyl oder für NR'R" steht, worin R' und R" unabhängig voneinander für einen Rest aus der Reihe Wasserstoff und C1-C4-Alkyl stehen,
R18
für einen Rest aus der Reihe Wasserstoff, Hydroxy, für jeweils gegebenenfalls einfach, zweifach, dreifach, vierfach oder fünffach durch Fluor, Chlor oder einfach oder zweifach durch Cyano substituiertes C1-C4-Alkyl, C1-C4-Alkoxy, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4-Alkyl-S-C1-C2-alkyl, C1-C4-Alkyl-S(O)-C1-C2-alkyl, C1-C4-Alkyl-S(O)2-C1-C2-alkyl, C1-C4-Alkylcarbonyl, C1-C4-Alkoxycarbonyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C3-alkyl, Heterocyclyl und Heterocyclyl-C1-C3-alkyl und jeweils gegebenenfalls einfach bis dreifach durch C1-C4-Alkyl, C1-C3-Halogenalkyl, C1-C3-Alkoxy, C1-C3-Halogenalkoxy, Cyclopropyl, Fluor, Chlor, Brom oder Cyano substituiertes Phenyl, Benzyl, Pyridyl, Pyrimidyl, Thiazolyl, Oxazolyl, Pyrazolyl, Thienyl, Furanyl, Pyridinylmethyl und Thiazolylmethyl steht,
R19
für Wasserstoff, ein Alkali- oder Erdalkalimetallion, für ein gegebenfalls einfach bis vierfach durch C1-C4-Alkyl substituiertes Ammoniumion oder für einen jeweils gegebenenfalls einfach, zweifach, dreifach, vierfach oder fünffach durch Fluor, Chlor oder einfach oder zweifach durch Cyano substituierten Rest aus der Reihe C1-C4-Alkyl, C1-C4-Alkoxy, C1-C4-Alkoxy-C1-C2-alkyl und C1-C4-Alkyl-S-C1-C2-alkyl, C1-C4-Alkyl-S(O)-C1-C2-alkyl und C1-C4-Alkyl-S(O)2-C1-C2-alkyl steht,
W
für einen Rest aus der Reihe S, SO und SO2 steht,
Y3
für einen Rest aus der Reihe Wasserstoff, Fluor, Chlor, Brom, Cyano, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy, Difluormethoxy und Trifluormethoxy steht,
R22
für einen Rest aus der Reihe Methyl, Ethyl, Isopropyl, n-Propyl, n-Butyl, iso-Butyl, sec-Butyl, tert-Butyl, 2,2,2-Trifluorethyl, 2,2-Difluorethyl, 2,2-Difluor-n-propyl, Methylsulfanyl-methyl, Methylsulfanylethyl, Methylsulfanyl-n-propyl, Trifluormethylsulfonylmethyl, Ethylsulfonylmethyl, 2,2,2-Trifluorethylsulfonylmethyl, 2,2-Difluorethylsulfonylmethyl, Isopropylsulfanylmethyl, Methylsulfinylmethyl, Trifluormethylsulfinylmethyl, Ethylsulfinylmethyl, 2,2,2-Trifluorethylsulfinylmethyl, 2,2-Difluorethylsulfinylmethyl, Isopropylsulfinylmethyl, Methylsulfonylmethyl, Trifluormethylsulfonylmethyl, Ethylsulfonylmethyl, 2,2,2-Trifluorethylsulfonylmethyl, 2,2-Difluorethylsulfonylmethyl, Isopropylsulfonylmethyl, Methoxycarbonyl, Ethoxycarbonyl, Methoxycarbonylmethyl, Ethoxycarbonylmethyl, Methoxycarbonylethyl, Ethoxycarbonylethyl, Dimethylaminocarbonyl, Diethylaminocarbonyl, N-Ethyl-N-methylaminocarbonyl, N-Isopropyl-N-methylaminocarbonyl, Dimethylaminocarbonylmethyl, Diethylaminocarbonylmethyl, N-Ethyl-N-methylaminocarbonylmethyl, N-Isopropyl-N-methylaminocarbonylmethyl, Dimethylaminocarbonylethyl, Diethylaminocarbonylethyl, N-Ethyl-N-methylaminocarbonylethyl, N-Isopropyl-N-methylaminocarbonylethyl, N-Cyclopropyl-N-methylaminocarbonylmethyl, N-Cyclopropyl-N-methylaminocarbonylethyl, Methylsulfanyl, Trifluormethylsulfanyl, Ethylsulfanyl, 2,2,2-Trifluorethylsulfanyl, 2,2-Difluorethylsulfanyl, Isopropylsulfanyl, Methylsulfinyl, Trifluormethylsulfinyl, Ethylsulfinyl, 2,2,2-Trifluorethylsulfinyl, 2,2-Difluorethylsulfinyl, Isopropylsulfinyl, Methylsulfonyl, Trifluormethylsulfonyl, Ethylsulfonyl, 2,2,2-Trifluorethylsulfonyl, 2,2-Difluorethylsulfonyl, Isopropylsulfonyl, Cyclopropyl, 1-Cyanocyclopropyl, 1-Chlorcyclopropyl, 1-Fluorcyclopropyl, 2-Cyanocyclopropyl, 2-Chlorcyclopropyl, 2-Fluorcyclopropyl, 2,2,3,3-Tetrafluorcyclopropyl, 2-Cyclopropylcyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, 4-Trifluormethylcyclohexyl, Cyclopropylmethyl, Cyclopropylethyl, Cyclobutylmethyl N-Cyclopropyl-N-methylaminocarbonyl Morpholin-4-ylcarbonylmethyl, Piperazin-1 -ylcarbonylmethyl, 4-Methyl-piperazin-1-ylcarbonylmethyl, jeweils gegebenenfalls einfach, zweifach oder dreifach, gleich oder verschieden durch Fluor, Chlor, Brom, Cyano, Nitro, Hydroxy, Amino, Methyl, Ethyl, Isopropyl, tert-Butyl, Trifluormethyl, Difluormethyl, Methoxy, Trifluormethoxy, Difluormethoxy substituiertes Heterocyclylmethyl und Heterocyclylethyl, jeweils durch Cyclopropyl substituiertes Heterocyclylmethyl und Heterocyclylethyl, wobei der Cyclopropylrest gegebenenfalls einfach oder zweifach durch Methyl, Fluor, Chlor, Cyano oder einfach durch Cyclopropyl substituiert ist, gegebenenfalls einfach, zweifach oder dreifach, gleich oder verschieden durch Fluor, Chlor, Brom, Cyano, Nitro, Hydroxy, Amino, Methyl, Ethyl, Isopropyl, tert-Butyl, Trifluormethyl, Difluormethyl, Methoxy, Trifluormethoxy, Difluormethoxy substituiertes Aryl, durch Cyclopropyl substituiertes Aryl, wobei der Cyclopropylrest gegebenenfalls einfach oder zweifach durch Methyl, Fluor, Chlor, Cyano oder einfach durch Cyclopropyl substituiert ist, jeweils gegebenenfalls einfach, zweifach oder dreifach, gleich oder verschieden durch Fluor, Chlor, Brom, Cyano, Nitro, Hydroxy, Amino, Methyl, Ethyl, Isopropyl, tert-Butyl, Trifluormethyl, Difluormethyl, Methoxy, Trifluormethoxy, Difluormethoxy substituiertes Arylmethyl und Arylethyl, durch Cyclopropyl substituiertes Arylmethyl und Arylethyl, wobei der Cyclopropylrest gegebenenfalls einfach oder zweifach durch Methyl, Fluor, Chlor, Cyano oder einfach durch Cyclopropyl substituiert ist, jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Fluor, Chlor, Brom, Cyano, Nitro, Hydroxy, Amino, Methyl, Ethyl, Isopropyl, tert-Butyl, Trifluormethyl, Difluormethyl, Methoxy, Trifluormethoxy, Difluormethoxy substituiertes Hetarylmethyl und Hetarylethyl, durch Cyclopropyl substituiertes Hetarylmethyl und Hetarylethyl, wobei der Cyclopropylrest gegebenenfalls einfach oder zweifach durch Methyl, Fluor, Chlor, Cyano oder einfach durch Cyclopropyl substituiert ist, steht, oder
R22
für einen D-Rest aus der Reihe (D-1) bis (D-3)
Figure imgb0213
 für einen der folgenden E-Reste
Figure imgb0214
Figure imgb0215
Figure imgb0216
Figure imgb0217
Figure imgb0218
 steht, oder im Fall R2 = d),
R22
auch für den Rest (E-13)
Figure imgb0219
 steht,
R23
für einen Rest aus der Reihe Wasserstoff, C1-C6-Alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkenyl, C1-C6-Alkoxy, C2-C6-Alkenyloxy, C2-C6-Alkinyloxy, C3-C6-Cycloalkyloxy, C1-C4-Alkylthio-C1-C4-alkyl, C2-C4-Alkenylthio-C1-C4-alkyl, Cyano-C1-C4-alkyl, C1-C4-Alkoxy-C1-C4alkyl steht,
oder, für R2 = c) oder g),
R22 und R23
auch gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, für Pyrrolidinyl, Piperidinyl, Morpholinyl, Thiomorpholinyl, Thiomorpholinyl-1-oxid, Thiomorpholinyl-1,1-dioxid, Piperazinyl, 1-Methylpiperazinyl oder 2-Oxo-1- methylpiperazinyl stehen,
R26
für einen Rest aus der Reihe Wasserstoff, Methyl, 2,2,2-Trifluorethyl, 2,2-Difluorethyl, Propenyl, Propargyl, Cyclopropyl, Cyclopropylmethyl, Methoxymethyl, Methylsulfanyl, Trifluormethylsulfanyl, Ethylsulfanyl, Trifluorethylsulfanyl, Methylsulfinyl, Trifluormethylsulfinyl, Ethylsulfinyl, Trifluorethylsulfinyl Methylthioethyl, Methylsulfinylethyl, Methylsulfonylethyl und Cyanomethyl steht und
R27
für Wasserstoff, Methyl, 2,2,2-Trifluorethyl, 2,2-Difluorethyl, Propenyl, Propargyl, Cyclopropyl, Cyclopropylmethyl, Methoxymethyl, Methylthioethyl, Methylsulfinylethyl, Methylsulfonylethyl oder Cyanomethyl steht und
Verbindungen der Formel (I), in welchen
A
für den A-Rest
Figure imgb0220
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet,
G1
für N oder C-B1 steht,
B1
für einen Rest aus der Reihe Wasserstoff und Fluor steht,
T
für Sauerstoff oder ein Elektronenpaar steht,
Q
für Schwefel setht,
R1
für Wasserstoff steht,
R2
für einen B-Rest aus der Reihe
Figure imgb0221
Figure imgb0222
Figure imgb0223
Figure imgb0224
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder
R2
c) für einen Rest der Formel
Figure imgb0225
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder
R2
d) für einen Rest der Formel
Figure imgb0226
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder
R2
e) für einen F-Rest aus der Reihe (F-8) und (F-10)
Figure imgb0227
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder
R2
f) für einen Rest aus der Reihe C1-C6-Halogenalkyl und Carboxyl steht, oder
R2
g) für einen Rest der Formel
Figure imgb0228
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, worin
G2
für Wasserstoff oder einen Rest aus der Reihe Halogen, Nitro, Amino, Cyano, C1-C4-Alkylamino, Halogen C1-C4-Alkylamino, Di-(C1-C4-alkyl)-amino, C1-C4-Alkyl, Halogen-C1-C4-alkyl, C1-C4-Alkoxy, Halogen-C1-C4-alkoxy, C1-C4-Alkoxy-C1-C4-alkyl, halogeniertes C1-C4-Alkoxy-C1-C4-alkyl, Bis(C1-C4-alkoxy)-C1-C4-alkyl, Bis(halogen-C1-C4-alkoxy)-C1-C4-alkyl, C1-C4-Alkoxy(C1-C4-alkylsulfanyl)-C1-C4-alkyl, C1-C4-Alkoxy(C1-C4-alkylsulfinyl)-C1-C4-alkyl, C1-C4-Alkoxy(C1-C4-alkylsulfonyl)-C1-C4-alkyl, Bis(C1-C4-alkylsulfanyl)-C1-C4-alkyl, Bis(halogen-C1-C4-alkylsulfanyl)-C1-C4-alkyl, Bis(hydroxy-C1-C4-alkylsulfanyl)-C1-C4-alkyl, C1-C4-Alkoxycarbonyl, C1-C4-Alkoxycarbonyl-C1-C4-alkyl, C(X2)NR3R4, NR6R7, C1-C4-Alkylthio, C1-C4-Alkylsulfinyl, C1-C4-Alkylsulfonyl, C1-C4-Halogenalkylthio, C1-C4-Halogenalkylsulfinyl und C1-C4-Halogenalkylsulfonyl steht, oder
G2
für einen Rest (C-1) oder (C-9)
Figure imgb0229
 steht, worin die gestrichelte Linie die Bindung zu den B-Resten bedeutet,
X
für Sauerstoff steht,
X2
für Sauerstoff, Schwefel, NR5 oder NOH steht,
n
für 2 steht,
R3
für C1-C4-Alkyl steht,
R4
für einen Rest aus der Reihe Wasserstoff, C1-C4-Alkyl, Halogen-C1-C4-alkyl, Cyano-C1-C4-alkyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C4-alkyl, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4-Alkoxycarbonyl, C1-C4-Alkoxycarbonyl-C1-C4-alkyl und C1-C4-Alkylthio-C1-C4-alkyl steht,
R5
für einen Rest aus der Reihe Wasserstoff, C1-C4-Alkyl, Halogen-C1-C4-alkyl, Cyano-C1-C4-alkyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C4-alkyl, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4-Alkoxycarbonyl, C1-C4-Alkoxycarbonyl-C1-C4-alkyl und C1-C4-Alkylthio-C1-C4-alkyl steht,
R6
für Wasserstoff oder C1-C4-Alkyl steht,
R7
für einen Rest aus der Reihe Wasserstoff, C1-C4-Alkyl, Halogen-C1-C4-alkyl, Cyano-C1-C4-alkyl, C2-C4-Alkinyl, C1-C4-Alkoxy, Halogen-C1-C4-alkoxy, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4-Alkoxycarbonyl, C1-C4-Alkoxycarbonyl-C1-C4-alkyl, C1-C4-Alkylthio-C1-C4-alkyl, Aryl-C1-C4-alkyl oder Hetaryl-C1-C4-alkyl steht oder
R6 und R7
gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen 4- bis 7-gliedrigen Ring bilden, der ein oder zwei weitere Heteroatome aus der Reihe Stickstoff, Sauerstoff und Schwefel (wobei Sauerstoff- und Schwefelatome nicht unmittelbar benachbart sein dürfen) enthalten kann,
R8
für einen Rest aus der Reihe Wasserstoff, C1-C6-Alkyl, C1-C6-Halogenalkyl, Cyano-C1-C6-alkyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C2-C6-Alkenyl, C1-C6-Alkoxy-C1-C6-alkyl, jeweils gegebenenfalls durch Halogen substituiertes C1-C6-Alkylcarbonyl und C1-C6-Alkylsulfonyl, gegebenenfalls durch Halogen substituiertes C1-C6-Alkoxycarbonyl, gegebenenfalls durch Halogen, C1-C6-Alkyl, C1-C6-Alkoxy, C1-C6-Halogenalkyl und Cyano substituiertes C3-C6-Cycloalkylcarbonyl, oder für ein Kation oder ein gegebenenfalls durch C1-C6-Alkyl oder Aryl-Ci-C6-alkyl substituiertes Ammonium-Ion steht,
R9
für einen Rest aus der Reihe jeweils gegebenenfalls durch Halogen, C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C1-C4-Alkylthio, C1-C4-Halogenalkylthio, C1-C4-Alkylsulfinyl, C1-C4-Halogenalkylsulfinyl, C1-C4-Alkylsulfonyl und C1-C4-Halogenalkylsulfonyl substituiertes C1-C4-Alkyl, C2-C4-Alkenyl und C2-C4-Alkinyl, jeweils gegebenenfalls durch Halogen, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy substituiertes C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C4-alkyl und C3-C4-Cycloalkenyl, in welchen ein oder zwei Ringglieder jeweils durch ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff ersetzt sein können (und dabei insbesondere für
Figure imgb0230
 wobei der Pfeil jeweils die Bindung zum S-Atom im Rest (C-1) markiert), jeweils gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, C1-C4-Alkyl, C1-C4-Halogenalkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C1-C4-Alkylthio, C1-C4-Halogenalkylthio, C1-C4-Alkylsulfinyl, C1-C4-Halogenalkylsulfinyl, C1-C4-Alkylsulfonyl, C1-C4-Halogenalkylsulfonyl, Amino, C1-C4-Alkylamino, Di-(C1-C4-alkyl)-amino, C1-C4-Alkylcarbonylamino, C1-C4-Alkoxycarbonylamino, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4-Halogenalkoxy-C1-C4-alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl-C1-C4-alkyl, C1-C4-Alkylcarbonyl, C1-C4-Alkoxycarbonyl oder Aminocarbonyl substituiertes Aryl, Heteroaryl, Aryl-C1-C4-alkyl und Heteroaryl-C1-C4-alkyl oder für NR'R" steht, worin R' und R" unabhängig voneinander für einen Rest aus der Reihe Wasserstoff und C1-C4-Alkyl stehen,
R8 und R9
können im Rest (C-1) auch zusammen mit der N-S(O)n Gruppe, an die sie gebunden sind, einen gesättigten oder ungesättigten und gegebenenfalls durch Halogen, C1-C6-Alkyl, C1-C6-Halogenalkyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy substituierten 5- bis 7-gliedrigen Ring bilden, der ein oder zwei Heteroatome aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff und/oder mindestens eine und bevorzugt eine Carbonylgruppe enthalten kann, insbesondere können R8 und R9 zusammen mit der N-S(O)n Gruppe, an die sie gebunden sind, für einen Rest aus der Reihe
Figure imgb0231
Figure imgb0232
 stehen (worin der Pfeil jeweils die Bindung zur C(X)-Gruppe markiert),
R17
für einen Rest aus der Reihe jeweils gegebenenfalls durch Halogen, C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C1-C4-Alkylthio, C1-C4-Halogenalkylthio, C1-C4-Alkylsulfinyl, C1-C4-Halogenalkylsulfinyl, C1-C4-Alkylsulfonyl und C1-C4-Halogenalkylsulfonyl substituiertes C1-C4-Alkyl, C2-C4-Alkenyl und C2-C4-Alkinyl, jeweils gegebenenfalls durch Halogen, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy substituiertes C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C4-alkyl und C3-C4-Cycloalkenyl, N-Pyrrolidinyl, N-Piperidinyl, N-Morpholinyl, N-Thiomorpholinyl, N-Thiomorpholinyl-1-oxid, N-Thiomorpholinyl-1,1-dioxid, N-Piperazinyl, N-1-Methylpiperazinyl oder N-2-Oxo-1-methylpiperazinyl, jeweils gegebenenfalls durch Halogen, Cyano (auch im Alkylteil), Nitro, C1-C4-Alkyl, C1-C4-Halogenalkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C1-C4-Alkylthio, C1-C4-Halogenalkylthio, C1-C4-Alkylsulfinyl, C1-C4-Halogenalkylsulfinyl, C1-C4-Alkylsulfonyl, C1-C4-Halogenalkylsulfonyl, Amino, C1-C4-Alkylamino, Di-(C1-C4-alkyl)-amino, C1-C4-Alkylcarbonylamino, C1-C4-Alkoxycarbonylamino, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4-Halogenalkoxy-C1-C4-alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl-C1-C4-alkyl, C1-C4-Alkylcarbonyl, C1-C4-Alkoxycarbonyl oder Aminocarbonyl substituiertes Aryl, Heteroaryl, Aryl-C1-C4-alkyl und Heteroaryl-C1-C4-alkyl oder für NR'R" steht, worin R' und R" unabhängig voneinander für einen Rest aus der Reihe Wasserstoff und C1-C4-Alkyl stehen,
und im Fall, dass R2 für g) steht,
R22
für einen Rest aus der Reihe Methyl, Ethyl, Isopropyl, n-Propyl, n-Butyl, iso-Butyl, sec-Butyl, tert-Butyl, 2,2,2-Trifluorethyl, 2,2-Difluorethyl, 2,2-Difluor-n-propyl, Methylsulfanyl-methyl, Methylsulfanylethyl, Methylsulfanyl-n-propyl, Trifluormethylsulfonylmethyl, Ethylsulfonylmethyl, 2,2,2-Trifluorethylsulfonylmethyl, 2,2-Difluorethylsulfonylmethyl, Isopropylsulfanylmethyl, Methylsulfinylmethyl, Trifluormethylsulfinylmethyl, Ethylsulfinylmethyl, 2,2,2-Trifluorethylsulfinylmethyl, 2,2-Difluorethylsulfinylmethyl, Isopropylsulfinylmethyl, Methylsulfonylmethyl, Trifluormethylsulfonylmethyl, Ethylsulfonylmethyl, 2,2,2-Trifluorethylsulfonylmethyl, 2,2-Difluorethylsulfonylmethyl, Isopropylsulfonylmethyl, Methoxycarbonylmethyl, Ethoxycarbonylmethyl, Methoxycarbonylethyl, Ethoxycarbonylethyl, Dimethylamino-carbonylmethyl, Diethylaminocarbonylmethyl, N-Ethyl-N-methylaminocarbonylmethyl, N-Isopropyl-N-methylaminocarbonylmethyl, Dimethylaminocarbonylethyl, Diethylamino-carbonylethyl, N-Ethyl-N-methylaminocarbonylethyl, N-Isopropyl-N-methylaminocarbonylethyl, N-Cyclopropyl-N-methylaminocarbonylmethyl, N-Cyclopropyl-N-methylaminocarbonylethyl, Methylsulfanyl, Trifluormethylsulfanyl, Ethylsulfanyl, 2,2,2-Trifluorethylsulfanyl, 2,2-Difluorethylsulfanyl, Isopropylsulfanyl, Methylsulfinyl, Trifluormethylsulfinyl, Ethylsulfinyl, 2,2,2-Trifluorethylsulfinyl, 2,2-Difluorethylsulfinyl, Isopropylsulfinyl, Methylsulfonyl, Trifluormethylsulfonyl, Ethylsulfonyl, 2,2,2-Trifluorethylsulfonyl, 2,2-Difluorethylsulfonyl, Isopropylsulfonyl, Cyclopropyl, 1-Cyanocyclopropyl, 1-Chlorcyclopropyl, 1-Fluorcyclopropyl, 2-Cyanocyclopropyl, 2-Chlorcyclopropyl, 2-Fluorcyclopropyl, 2,2,3,3-Tetrafluorcyclopropyl, 2-Cyclopropylcyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, 4-Trifluormethylcyclohexyl, Cyclopropylmethyl, Cyclopropylethyl, Cyclobutylmethyl, Morpholin-4-ylcarbonylmethyl, Piperazin-1-ylcarbonylmethyl, 4-Methyl-piperazin-1-ylcarbonylmethyl, jeweils gegebenenfalls einfach, zweifach oder dreifach, gleich oder verschieden durch Fluor, Chlor, Brom, Cyano, Nitro, Hydroxy, Amino, Methyl, Ethyl, Isopropyl, tert-Butyl, Trifluormethyl, Difluormethyl, Methoxy, Trifluormethoxy, Difluormethoxy substituiertes Heterocyclylmethyl und Heterocyclylethyl, jeweils durch Cyclopropyl substituiertes Heterocyclylmethyl und Heterocyclylethyl, wobei der Cyclopropylrest gegebenenfalls einfach oder zweifach durch Methyl, Fluor, Chlor, Cyano oder einfach durch Cyclopropyl substituiert ist, gegebenenfalls einfach, zweifach oder dreifach, gleich oder verschieden durch Fluor, Chlor, Brom, Cyano, Nitro, Hydroxy, Amino, Methyl, Ethyl, Isopropyl, tert-Butyl, Trifluormethyl, Difluormethyl, Methoxy, Trifluormethoxy, Difluormethoxy substituiertes Aryl, durch Cyclopropyl substituiertes Aryl, wobei der Cyclopropylrest gegebenenfalls einfach oder zweifach durch Methyl, Fluor, Chlor, Cyano oder einfach durch Cyclopropyl substituiert ist, jeweils gegebenenfalls einfach, zweifach oder dreifach, gleich oder verschieden durch Fluor, Chlor, Brom, Cyano, Nitro, Hydroxy, Amino, Methyl, Ethyl, Isopropyl, tert-Butyl, Trifluormethyl, Difluormethyl, Methoxy, Trifluormethoxy, Difluormethoxy substituiertes Arylmethyl und Arylethyl, durch Cyclopropyl substituiertes Arylmethyl und Arylethyl, wobei der Cyclopropylrest gegebenenfalls einfach oder zweifach durch Methyl, Fluor, Chlor, Cyano oder einfach durch Cyclopropyl substituiert ist, jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Fluor, Chlor, Brom, Cyano, Nitro, Hydroxy, Amino, Methyl, Ethyl, Isopropyl, tert-Butyl, Trifluormethyl, Difluormethyl, Methoxy, Trifluormethoxy, Difluormethoxy substituiertes Hetarylmethyl und Hetarylethyl, durch Cyclopropyl substituiertes Hetarylmethyl und Hetarylethyl, wobei der Cyclopropylrest gegebenenfalls einfach oder zweifach durch Methyl, Fluor, Chlor, Cyano oder einfach durch Cyclopropyl substituiert ist, steht, und im Fall, dass R2 für c), d) oder g) steht,
R22
für einen D-Rest aus der Reihe (D-1) bis (D-3)
Figure imgb0233
 worin
X1
für einen Rest aus der Reihe Wasserstoff, Fluor, Chlor, Brom, Cyano, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy, Difluormethoxy und Trifluormethoxy steht,
R
für NR18R19 oder für einen jeweils gegebenfalls einfach, zweifach, dreifach, vierfach oder fünffach durch Fluor, Chlor oder einfach oder zweifach durch Cyano substituierten Rest aus der Reihe C1-C4-Alkyl, C3-C4-Alkenyl, C3-C4-Alkinyl, C1-C2-Alkoxy-C1-C2-alkyl und C1-C2-Alkyl-S-C1-C2-alkyl, C1-C2-Alkyl-S(O)-C1-C2-alkyl, C1-C2-Alkyl-S(O)2-C1-C2-alkyl, für R18-CO-C1-C2-alkyl, für NR18R19-CO-C1-C2-alkyl, für gegebenenfalls einfach oder zweifach durch C1-C2-Alkyl, C1-C2-Alkoxy oder C1-C2-Halogenalkyl oder durch ein Sauerstoffatom (führt zu C=O) substituiertes C3-C6-Cycloalkyl, für gegebenenfalls einfach oder zweifach durch C1-C2-Alkyl, C1-C2-Alkoxy oder C1-C2-Halogenalkyl oder durch ein Sauerstoffatom (führt zu C=O) substituiertes C3-C6-Cycloalkenyl, für gegebenenfalls einfach bis zweifach durch C1-C2-Alkyl, C1-C2-Alkoxy oder C1-C2-Halogenalkyl substituiertes C3-C6-Cycloalkyl-C1-C2-alkyl, für gegebenenfalls einfach oder zweifach durch C1-C2-Alkyl, C1-C2-Alkoxy oder C1-C2-Halogenalkyl substituiertes C3-C6-Cycloalkenyl-C1-C2-alkyl, für gegebenenfalls einfach oder zweifach durch C1-C2-Alkyl, C1-C2-Alkoxy oder C1-C2-Halogenalkyl substituiertes Heterocyclyl, für gegebenenfalls einfach oder zweifach durch C1-C2-Alkyl, C1-C2-Alkoxy oder C1-C2-Halogenalkyl substituiertes Heterocyclyl-C1-C2-alkyl oder für jeweils gegebenenfalls einfach oder zweifach durch Fluor, Chlor, Brom, Cyano, Methyl, Ethyl, Difluormethyl, Trifluormethyl, Methoxy, Ethoxy, Difluormethoxy oder Trifluormethoxy substituiertes Phenyl, Benzyl, Pyridyl, Pyrimidyl, Thiazolyl, Oxazolyl, Pyrazolyl, Thienyl, Furanyl, Pyridinylmethyl oder Thiazolylmethyl steht,
W
für einen Rest aus der Reihe S, SO und SO2 steht,
Y3
für einen Rest aus der Reihe Wasserstoff, Fluor, Chlor, Brom, Cyano, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy, Difluormethoxy und Trifluormethoxy steht,
R22
ferner für einen der folgenden E-Reste
Figure imgb0234
Figure imgb0235
Figure imgb0236
Figure imgb0237
Figure imgb0238
 steht, oder im Fall R2 = d),
R22
auch für den Rest (E-13)
Figure imgb0239
 steht,
R18
für einen Rest aus der Reihe Wasserstoff, Hydroxy, für jeweils gegebenenfalls einfach, zweifach, dreifach, vierfach oder fünffach durch Fluor, Chlor oder einfach oder zweifach durch Cyano substituiertes C1-C4-Alkyl, C1-C4-Alkoxy, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4-Alkyl-S-C1-C2-alkyl, C1-C4-Alkyl-S(O)-C1-C2-alkyl, C1-C4-Alkyl-S(O)2-C1-C2-alkyl, C1-C4-Alkylcarbonyl, C1-C4-Alkoxycarbonyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyl-C1-C3-alkyl, Heterocyclyl und Heterocyclyl-C1-C3-alkyl und jeweils gegebenenfalls einfach bis dreifach durch C1-C4-Alkyl, C1-C3-Halogenalkyl, C1-C3-Alkoxy, C1-C3-Halogenalkoxy, Cyclopropyl, Fluor, Chlor, Brom oder Cyano substituiertes Phenyl, Benzyl, Pyridyl, Pyrimidyl, Thiazolyl, Oxazolyl, Pyrazolyl, Thienyl, Furanyl, Pyridinylmethyl und Thiazolylmethyl steht,
R19
für Wasserstoff, ein Alkali- oder Erdalkalimetallion, für ein gegebenfalls einfach bis vierfach durch C1-C4-Alkyl substituiertes Ammoniumion oder für einen jeweils gegebenenfalls einfach, zweifach, dreifach, vierfach oder fünffach durch Fluor, Chlor oder einfach oder zweifach durch Cyano substituierten Rest aus der Reihe C1-C4-Alkyl, C1-C4-Alkoxy, C1-C4-Alkoxy-C1-C2-alkyl und C1-C4-Alkyl-S-C1-C2-alkyl, C1-C4-Alkyl-S(O)-C1-C2-alkyl und C1-C4-Alkyl-S(O)2-C1-C2-alkyl steht,
R23
für einen Rest aus der Reihe Wasserstoff, C1-C6-Alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkenyl, C1-C6-Alkoxy, C2-C6-Alkenyloxy, C2-C6-Alkinyloxy, C3-C6-Cycloalkyloxy, C1-C4-Alkylthio-C1-C4-alkyl, C2-C4-Alkenylthio-C1-C4-alkyl, Cyano-C1-C4-alkyl, C1-C4-Alkoxy-C1-C4alkyl steht,
oder, für R2 = g),
R22 und R23
auch gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, für Pyrrolidinyl, Piperidinyl, Morpholinyl, Thiomorpholinyl, Thiomorpholinyl-1-oxid, Thiomorpholinyl-1,1-dioxid, Piperazinyl, 1-Methylpiperazinyl oder 2-Oxo-1-methylpiperazinyl stehen,
R26
für einen Rest aus der Reihe Wasserstoff, Methyl, 2,2,2-Trifluorethyl, 2,2-Difluorethyl, Propenyl, Propargyl, Cyclopropyl, Cyclopropylmethyl, Methoxymethyl, Methylsulfanyl, Trifluormethylsulfanyl, Ethylsulfanyl, Trifluorethylsulfanyl, Methylsulfinyl, Trifluormethylsulfinyl, Ethylsulfinyl, Trifluorethylsulfinyl Methylthioethyl, Methylsulfinylethyl, Methylsulfonylethyl und Cyanomethyl steht und
R27
für einen Rest aus der Reihe Wasserstoff, Methyl, 2,2,2-Trifluorethyl, 2,2-Difluorethyl, Propenyl, Propargyl, Cyclopropyl, Cyclopropylmethyl, Methoxymethyl, Methylthioethyl, Methylsulfinylethyl, Methylsulfonylethyl und Cyanomethyl steht.
Preferred range (3): Very particular preference is given to compounds of the formula (I) in which
A
for an A-residue from the series (Ab) and (Af)
Figure imgb0199
 in which the dashed line denotes the bond to the carbon atom of the bicyclic compound of the formula (I),
B 2
stands for hydrogen,
Q
for sulfur setht,
R 1
stands for hydrogen,
R 2
for a B-rest from the series
Figure imgb0200
Figure imgb0201
Figure imgb0202
Figure imgb0203
 wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R 2
b) for a D radical from the series (D-1) to (D-3)
Figure imgb0204
 wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R 2
c) a radical of the formula
Figure imgb0205
 wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R 2
d) for a radical of the formula
Figure imgb0206
 wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R 2
e) for an F radical from the series (F-1), (F-8) and (F-10)
Figure imgb0207
 wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R 2
f) is a radical from the series C 1 -C 6 -haloalkyl and carboxyl, or
R 2
g) for a radical of the formula
Figure imgb0208
 wherein the dotted line represents the bond to the carbon atom of the bicyclic moiety of formula (I) wherein
G 2
is hydrogen or a radical from the series halogen, nitro, amino, cyano, C 1 -C 4 -alkylamino, halogen C 1 -C 4 -alkylamino, di- (C 1 -C 4 -alkyl) -amino, C 1 - C 4 alkyl, haloC 1 -C 4 alkyl, C 1 -C 4 alkoxy, Halogeno-C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, halogenated C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, bis (C 1 -C 4 -alkoxy) -C 1 -C 4 -alkyl, bis (haloC 1 -C 4 -alkoxy) -C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy (C 1 -C 4 -alkylsulfanyl) - C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy (C 1 -C 4 -alkylsulfinyl) C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy (C 1 -C 4 -alkylsulfonyl) - C 1 -C 4 alkyl, bis (C 1 -C 4 alkylsulfanyl) C 1 -C 4 alkyl, bis (haloC 1 -C 4 alkylsulfanyl) C 1 -C 4 alkyl, bis ( hydroxy-C 1 -C 4 -alkylsulfanyl) C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl, C (X 2 ) NR 3 R 4, NR 6 R 7, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylthio, C 1 -C 4 haloalkylsulfinyl and C 1 C 4 haloalkylsulfonyl, or
G 2
for a C-radical (C-1) or (C-9)
Figure imgb0209
 wherein the dashed line indicates the bond to the B radicals,
X
stands for oxygen,
X 1
a radical selected from the group consisting of hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy and trifluoromethoxy,
X 2
is oxygen, sulfur, NR 5 or NOH,
n
stands for 2,
R
for NR 18 R 19 or for any given mono-, di-, tri-, tetra- or quintuply fluorine, chlorine or mono- or di-cyano-substituted radical from the series C 1 -C 4 -alkyl, C 3 -C 4 -alkenyl, C 3 -C 4 -alkynyl, C 1 -C 2 -alkoxy-C 1 -C 2 -alkyl and C 1 -C 2 -alkyl-SC 1 -C 2 -alkyl, C 1 -C 2 -alkyl-S ( O) -C 1 -C 2 -alkyl, C 1 -C 2 -alkyl-S (O) 2 -C 1 -C 2 -alkyl, for R 18 -CO-C 1 -C 2 -alkyl, for NR 18 R 19 is -CO-C 1 -C 2 -alkyl, optionally optionally mono- or disubstituted by C 1 -C 2 -alkyl, C 1 -C 2 -alkoxy or C 1 -C 2 -haloalkyl or by an oxygen atom (leads to C = O) substituted C 3 -C 6 -cycloalkyl, optionally optionally mono- or disubstituted by C 1 -C 2 -alkyl, C 1 -C 2 -alkoxy or C 1 -C 2 -haloalkyl or by an oxygen atom (leads to C = O) substituted C 3 -C 6 -cycloalkenyl, optionally mono- to disubstituted by C 1 -C 2 -alkyl, C 1 -C 2 -alkoxy or C 1 -C 2 -haloalkyl-substituted C 3 -C 6 -cycloal C 1 -C 2 -alkyl, C 3 -C 6 -cycloalkenyl-C 1 which is optionally monosubstituted or disubstituted by C 1 -C 2 -alkyl, C 1 -C 2 -alkoxy or C 1 -C 2 -haloalkyl C 2 -alkyl, heterocyclyl which is optionally monosubstituted or disubstituted by C 1 -C 2 -alkyl, C 1 -C 2 -alkoxy or C 1 -C 2 -haloalkyl and is optionally mono- or disubstituted by C 1 -C 2 - Alkyl, C 1 -C 2 -alkoxy or C 1 -C 2 -haloalkyl-substituted heterocyclyl-C 1 -C 2 -alkyl or phenyl optionally substituted once or twice by fluorine, chlorine, bromine, cyano, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy, benzyl, pyridyl, pyrimidyl, thiazolyl, oxazolyl, pyrazolyl, thienyl, furanyl, Pyridinylmethyl or thiazolylmethyl,
R 3
is C 1 -C 4 -alkyl,
R 4
a radical selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 2 -C 4 -alkynyl, C 3 -C 6 - Cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl- C 1 -C 4 -alkyl and C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl,
R 5
a radical selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 2 -C 4 -alkynyl, C 3 -C 6 - Cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl- C 1 -C 4 -alkyl and C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl,
R 6
is hydrogen or C 1 -C 4 -alkyl,
R 7
a radical selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 2 -C 4 -alkynyl, C 1 -C 4 - Alkoxy, halo-C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 - alkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, aryl-C 1 -C 4 -alkyl or hetaryl-C 1 -C 4 -alkyl or
R 6 and R 7
together with the nitrogen atom to which they are attached form a 4- to 7-membered ring which may contain one or two further nitrogen, oxygen and sulfur heteroatoms (oxygen and sulfur atoms not being immediately adjacent);
R 8
a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, cyano-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, in each case optionally halogen-substituted C 1 -C 6 -alkylcarbonyl and C 1 -C 6 -alkylsulfonyl, optionally C-substituted by halogen 1 -C 6 alkoxycarbonyl, optionally substituted by halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and cyano-substituted C 3 -C 6 cycloalkylcarbonyl, or a cation or 6 is an optionally alkyl or aryl-Ci-C 6 alkyl-substituted ammonium ion by C 1 -C
R 9
in each case a halogen radical, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfinyl , C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl and C 1 -C 4 -haloalkylsulfonyl-substituted C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl and C 2 -C 4 -alkynyl, respectively C 3 -C 6 -cycloalkyl optionally substituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 3 -C 6 - Cycloalkyl-C 1 -C 4 -alkyl and C 3 -C 4 -cycloalkenyl in which one or two ring members each by a heteroatom from the series sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen may be replaced (and in particular for
Figure imgb0210
 wherein the arrow in each case marks the bond to the S atom in the radical (C-1) and in the radical (F-1)), in each case optionally by halogen, cyano (also in the alkyl part), nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 C 4 alkylsulfinyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, amino, C 1 -C 4 alkylamino, di (C 1 -C 4 alkyl ) -amino, C 1 -C 4 -alkylcarbonylamino, C 1 -C 4 -alkoxycarbonylamino, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -haloalkoxy-C 1 -C 4 - alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl or Aminocarbonyl-substituted aryl, heteroaryl, aryl-C 1 -C 4 -alkyl and heteroaryl-C 1 -C 4 -alkyl or NR'R ", wherein R 'and R" are independently of one another a radical from the series of hydrogen and C 1 -C 4 -alkyl,
R 8 and R 9
in the radical (C-1) and in the radical (F-1), together with the NS (O) n group to which they are attached, a saturated or unsaturated and optionally halogen, C 1 -C 6 -alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy substituted 5- to 7-membered ring forming one or two heteroatoms selected from sulfur, oxygen (oxygen atoms not immediately adjacent may contain) and nitrogen and / or at least one and preferably a carbonyl group, in particular R 8 and R 9 together with the NS (O) n group to which they are attached, may be a radical from the series
Figure imgb0211
Figure imgb0212
 (in which the arrow in each case marks the bond to the C (X) group),
R 17
in each case a halogen radical, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfinyl , C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl and C 1 -C 4 -haloalkylsulfonyl-substituted C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl and C 2 -C 4 -alkynyl, each optionally substituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 Haloalkoxy-substituted C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl and C 3 -C 4 -cycloalkenyl, N-pyrrolidinyl, N-piperidinyl, N-morpholinyl, N-thiomorpholinyl , N-thiomorpholinyl-1-oxide, N-thiomorpholinyl-1,1-dioxide, N-piperazinyl, N-1-methylpiperazinyl or N-2-oxo-1-methylpiperazinyl, in each case optionally by halogen, cyano (also in the alkyl part) , Nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio , C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylsulfonyl, amino, C 1 -C 4 -alkylamino , Di- (C 1 -C 4 -alkyl) amino, C 1 -C 4 -alkylcarbonylamino, C 1 -C 4 -alkoxycarbonylamino, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 - C 4 haloalkoxy-C 1 -C 4 -alkyl, C 2 -C 4 - Alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl or aminocarbonyl-substituted aryl, heteroaryl, aryl- C 1 -C 4 -alkyl and heteroaryl-C 1 -C 4 -alkyl or NR'R ", in which R 'and R" independently of one another represent a radical from the series consisting of hydrogen and C 1 -C 4 -alkyl,
R 18
a radical selected from the group consisting of hydrogen, hydroxyl, in each case optionally mono-, di-, tri-, tetra- or trisubstituted by fluorine, chlorine or mono- or di-cyano-substituted C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkyl-C 1 -C 2 -alkyl, C 1 -C 4 -alkyl-S (O) -C 1 -C 2 - alkyl, C 1 -C 4 -alkyl-S (O) 2 -C 1 -C 2 -alkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 3 -alkyl, heterocyclyl and heterocyclyl-C 1 -C 3 -alkyl and in each case optionally mono- to trisubstituted by C 1 -C 4 -alkyl, C 1 -C 3 -haloalkyl, C 1 C 3 alkoxy, C 1 -C 3 haloalkoxy, cyclopropyl, fluorine, chlorine, bromine or cyano substituted phenyl, benzyl, pyridyl, pyrimidyl, thiazolyl, oxazolyl, pyrazolyl, thienyl, furanyl, pyridinylmethyl and thiazolylmethyl,
R 19
is hydrogen, an alkali or alkaline earth metal ion, an optionally mono- to quadruple C 1 -C 4 alkyl-substituted ammonium ion or each optionally optionally mono-, di-, tri-, tetra- or trisubstituted by fluorine, chlorine or mono- or disubstituted cyano Radical from the series C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl and C 1 -C 4 -alkyl-SC 1 -C 2 - alkyl, C 1 -C 4 -alkyl-S (O) -C 1 -C 2 -alkyl and C 1 -C 4 -alkyl-S (O) 2 -C 1 -C 2 -alkyl,
W
is a radical from the series S, SO and SO 2 ,
Y 3
a radical selected from the group consisting of hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy and trifluoromethoxy,
R 22
a radical from the series methyl, ethyl, isopropyl, n-propyl, n-butyl, isobutyl, sec-butyl, tert- butyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, 2,2- Difluoro-n-propyl, methylsulfanylmethyl, methylsulfanylethyl, methylsulfanyl-n-propyl, trifluoromethylsulfonylmethyl, Ethylsulfonylmethyl, 2,2,2-trifluoroethylsulfonylmethyl, 2,2-difluoroethylsulfonylmethyl, isopropylsulfanylmethyl, methylsulfinylmethyl, trifluoromethylsulfinylmethyl, ethylsulfinylmethyl, 2,2,2-trifluoroethylsulfinylmethyl, 2,2-difluoroethylsulfinylmethyl, isopropylsulfinylmethyl, methylsulfonylmethyl, trifluoromethylsulfonylmethyl, ethylsulfonylmethyl, 2,2, 2-Trifluorethylsulfonylmethyl, 2,2-Difluorethylsulfonylmethyl, Isopropylsulfonylmethyl, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, methoxycarbonylethyl, ethoxycarbonylethyl, dimethylaminocarbonyl, diethylaminocarbonyl, N-ethyl-N -methylaminocarbonyl, N -Isopropyl- N -methylaminocarbonyl, dimethylaminocarbonylmethyl, diethylaminocarbonylmethyl, N - ethyl N -methylaminocarbonylmethyl, N-isopropyl-N -methylaminocarbonylmethyl, Dimethylaminocarbonylethyl, Diethylaminocarbonylethyl, N -ethyl- N -methylaminocarbonylethyl, N -Isopropyl- N -methylaminocarbonylethyl, N -cyclopropyl N -methylaminocarbonylmeth yl, N- cyclopropyl- N- methylaminocarbonylethyl, methylsulfanyl, trifluoromethylsulfanyl, ethylsulfanyl, 2,2,2-trifluoroethylsulfanyl, 2,2-difluoroethylsulfanyl, isopropylsulfanyl, methylsulfinyl, trifluoromethylsulfinyl, ethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 2,2- Difluoroethylsulfinyl, isopropylsulfinyl, methylsulfonyl, trifluoromethylsulfonyl, ethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 2,2-difluoroethylsulfonyl, isopropylsulfonyl, cyclopropyl, 1-cyanocyclopropyl, 1-chlorocyclopropyl, 1-fluorocyclopropyl, 2-cyanocyclopropyl, 2-chlorocyclopropyl, 2- Fluorocyclopropyl, 2,2,3,3-tetrafluorocyclopropyl, 2-cyclopropylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-trifluoromethylcyclohexyl, cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, N- cyclopropyl- N- methylaminocarbonyl, morpholin-4-ylcarbonylmethyl, piperazine-1-ylcarbonylmethyl, 4-methylpiperazin-1-ylcarbonylmethyl, in each case optionally mono-, di- or trisubstituted, identically or differently, by fluorine, chlorine, bromine, cyano, nit ro, hydroxy, amino, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, trifluoromethoxy, difluoromethoxy-substituted heterocyclylmethyl and heterocyclylethyl, in each case cyclopropyl-substituted heterocyclylmethyl and heterocyclylethyl, where the cyclopropyl radical is optionally mono- or disubstituted by methyl, fluorine, Chloro, cyano or is simply substituted by cyclopropyl, optionally mono-, di- or trisubstituted by identical or different fluorine, chlorine, bromine, cyano, nitro, hydroxy, amino, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy Trifluoromethoxy, difluoromethoxy-substituted aryl, cyclopropyl-substituted aryl, where the cyclopropyl radical is optionally monosubstituted or disubstituted by methyl, fluorine, chlorine, cyano or simply by cyclopropyl, in each case optionally mono-, di- or trisubstituted, identically or differently, by fluorine, chlorine, Bromine, cyano, nitro, hydroxy, amino, meth yl, ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, trifluoromethoxy, difluoromethoxy-substituted arylmethyl and arylethyl, cyclopropyl-substituted arylmethyl and arylethyl, where the cyclopropyl radical optionally mono- or di-methyl, fluoro, chloro, cyano or simply cyclopropyl is optionally substituted once or twice, the same or different substituted by fluorine, chlorine, bromine, cyano, nitro, hydroxy, amino, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, trifluoromethoxy, difluoromethoxy substituted hetarylmethyl and hetarylethyl, substituted by cyclopropyl hetarylmethyl and hetarylethyl, wherein the cyclopropyl optionally is simply or disubstituted by methyl, fluorine, chlorine, cyano or simply substituted by cyclopropyl, or
R 22
for a D radical from the series (D-1) to (D-3)
Figure imgb0213
 for one of the following E radicals
Figure imgb0214
Figure imgb0215
Figure imgb0216
Figure imgb0217
Figure imgb0218
 or in case R 2 = d),
R 22
also for the rest (E-13)
Figure imgb0219
 stands,
R 23
a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 1 -C 6 alkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy, C 3 -C 6 cycloalkyloxy, C 1 -C 4 alkylthio-C 1 -C 4 alkyl, C 2 -C 4- alkenylthio-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl,
or, for R 2 = c) or g),
R 22 and R 23
also together with the nitrogen atom to which they are attached are pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, thiomorpholinyl-1-oxide, thiomorpholinyl-1,1-dioxide, piperazinyl, 1-methylpiperazinyl or 2-oxo-1-methylpiperazinyl,
R 26
a radical selected from the group consisting of hydrogen, methyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, propenyl, propargyl, cyclopropyl, cyclopropylmethyl, methoxymethyl, methylsulfanyl, trifluoromethylsulfanyl, ethylsulfanyl, trifluoroethylsulfanyl, methylsulfinyl, trifluoromethylsulfinyl, ethylsulfinyl, trifluoroethylsulfinyl, methylthioethyl , Methylsulfinylethyl, methylsulfonylethyl and cyanomethyl and
R 27
is hydrogen, methyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, propenyl, propargyl, cyclopropyl, cyclopropylmethyl, methoxymethyl, methylthioethyl, methylsulfinylethyl, methylsulfonylethyl or cyanomethyl and
Compounds of the formula (I) in which
A
for the A-rest
Figure imgb0220
 in which the dashed line denotes the bond to the carbon atom of the bicyclic compound of the formula (I),
G 1
stands for N or CB 1 ,
B 1
is a radical from the series hydrogen and fluorine,
T
stands for oxygen or a pair of electrons,
Q
for sulfur setht,
R 1
stands for hydrogen,
R 2
for a B-rest from the series
Figure imgb0221
Figure imgb0222
Figure imgb0223
Figure imgb0224
 wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R 2
c) a radical of the formula
Figure imgb0225
 wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R 2
d) for a radical of the formula
Figure imgb0226
 wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R 2
e) for an F radical from the series (F-8) and (F-10)
Figure imgb0227
 wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R 2
f) is a radical from the series C 1 -C 6 -haloalkyl and carboxyl, or
R 2
g) for a radical of the formula
Figure imgb0228
 wherein the dotted line represents the bond to the carbon atom of the bicyclic moiety of formula (I) wherein
G 2
is hydrogen or a radical from the series halogen, nitro, amino, cyano, C 1 -C 4 -alkylamino, halogen C 1 -C 4 -alkylamino, di- (C 1 -C 4 -alkyl) -amino, C 1 - C 4 alkyl, halo-C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halo-C 1 -C 4 alkoxy, C 1 -C 4 alkoxy-C 1 -C 4 alkyl, halogenated C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, bis (C 1 -C 4 -alkoxy) C 1 -C 4 -alkyl, bis (halogeno-C 1 -C 4 -alkoxy) -C 1 -C 4 alkyl, C 1 -C 4 alkoxy (C 1 -C 4 alkylsulfanyl) C 1 -C 4 alkyl, C 1 -C 4 alkoxy (C 1 -C 4 alkylsulfinyl) -C 1 -C 4 alkyl, C 1 -C 4 alkoxy (C 1 -C 4 alkylsulfonyl) C 1 -C 4 alkyl, bis (C 1 -C 4 alkylsulfanyl) C 1 -C 4 alkyl, Bis (halogeno-C 1 -C 4 -alkylsulfanyl) C 1 -C 4 -alkyl, bis (hydroxy-C 1 -C 4 -alkylsulfanyl) C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl, C (X 2 ) NR 3 R 4 , NR 6 R 7 , C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfinyl, C 1 - C 4 alkylsulfonyl, C 1 -C 4 haloalkylthio, C 1 -C 4 -haloalkylsulfinyl and C 1 -C 4 -haloalkylsulfo nyl stands, or
G 2
for a radical (C-1) or (C-9)
Figure imgb0229
 wherein the dashed line indicates the bond to the B radicals,
X
stands for oxygen,
X 2
is oxygen, sulfur, NR 5 or NOH,
n
stands for 2,
R 3
is C 1 -C 4 -alkyl,
R 4
a radical selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 2 -C 4 -alkynyl, C 3 -C 6 - Cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl- C 1 -C 4 -alkyl and C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl,
R 5
a radical selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 2 -C 4 -alkynyl, C 3 -C 6 - Cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl- C 1 -C 4 -alkyl and C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl,
R 6
is hydrogen or C 1 -C 4 -alkyl,
R 7
a radical selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 2 -C 4 -alkynyl, C 1 -C 4 - Alkoxy, halo-C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 - alkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, aryl-C 1 -C 4 -alkyl or hetaryl-C 1 -C 4 -alkyl or
R 6 and R 7
together with the nitrogen atom to which they are attached form a 4- to 7-membered ring which may contain one or two further nitrogen, oxygen and sulfur heteroatoms (oxygen and sulfur atoms not being immediately adjacent);
R 8
a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, cyano-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, in each case optionally halogen-substituted C 1 -C 6 -alkylcarbonyl and C 1 -C 6 -alkylsulfonyl, optionally C-substituted by halogen 1 -C 6 alkoxycarbonyl, optionally substituted by halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl and cyano-substituted C 3 -C 6 cycloalkylcarbonyl, or a cation or 6 is an optionally alkyl or aryl-Ci-C 6 alkyl-substituted ammonium ion by C 1 -C
R 9
in each case a halogen radical, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfinyl , C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl and C 1 -C 4 -haloalkylsulfonyl-substituted C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl and C 2 -C 4 -alkynyl, respectively C 3 -C 6 -cycloalkyl optionally substituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 3 -C 6 - Cycloalkyl-C 1 -C 4 -alkyl and C 3 -C 4 -cycloalkenyl in which one or two ring members in each case by a heteroatom selected from the group sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen may be replaced (and especially for
Figure imgb0230
 wherein the arrow in each case marks the bond to the S atom in the radical (C-1)), in each case optionally by halogen, cyano (also in the alkyl part), nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylsulfonyl, amino, C 1 -C 4 -alkylamino, di (C 1 -C 4 -alkyl) -amino, C 1 -C 4- alkylcarbonylamino, C 1 -C 4 -alkoxycarbonylamino, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -haloalkoxy-C 1 -C 4 -alkyl, C 2 -C 4 - Alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl or aminocarbonyl-substituted aryl, heteroaryl, aryl- C 1 -C 4 -alkyl and heteroaryl-C 1 -C 4 -alkyl or NR'R ", in which R 'and R" independently of one another represent a radical from the series consisting of hydrogen and C 1 -C 4 -alkyl,
R 8 and R 9
in the radical (C-1) also together with the NS (O) n group to which they are attached, a saturated or unsaturated and optionally halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy substituted 5- to 7-membered ring forming one or two heteroatoms selected from sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen and / or at least one and preferably a carbonyl group may contain, in particular R 8 and R 9 together with the NS (O) n group to which they are attached, a residue from the series
Figure imgb0231
Figure imgb0232
 (in which the arrow in each case marks the bond to the C (X) group),
R 17
in each case a halogen radical, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfinyl , C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl and C 1 -C 4 -haloalkylsulfonyl-substituted C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl and C 2 -C 4 -alkynyl, respectively C 3 -C 6 -cycloalkyl optionally substituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 3 -C 6 - Cycloalkyl-C 1 -C 4 -alkyl and C 3 -C 4 -cycloalkenyl, N-pyrrolidinyl, N-piperidinyl, N-morpholinyl, N-thiomorpholinyl, N-thiomorpholinyl-1-oxide, N-thiomorpholinyl-1,1- dioxide, N-piperazinyl, N-1-methylpiperazinyl or N-2-oxo-1-methylpiperazinyl, in each case optionally by halogen, cyano (also in the alkyl part), nitro, C 1 -C 4 -alkyl, C 1 -C 4 - Haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 1 C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, amino, C 1 -C 4 alkylamino, di (C 1 -C 4 alkyl) amino, C 1 -C 4 alkylcarbonylamino, C 1 -C 4- alkoxycarbonylamino, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -haloalkoxy-C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 - Alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl or aminocarbonyl-substituted aryl, heteroaryl, aryl-C 1 -C 4 -alkyl and Heteroaryl-C 1 -C 4 -alkyl or NR'R ", in which R 'and R" independently of one another represent a radical from the series consisting of hydrogen and C 1 -C 4 -alkyl,
and in the case where R 2 is g),
R 22
a radical from the series methyl, ethyl, isopropyl, n-propyl, n-butyl, isobutyl, sec-butyl, tert- butyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, 2,2- Difluoro-n-propyl, methylsulfanylmethyl, methylsulfanylethyl, methylsulfanyl-n-propyl, trifluoromethylsulfonylmethyl, ethylsulfonylmethyl, 2,2,2-trifluoroethylsulfonylmethyl, 2,2-difluoroethylsulfonylmethyl, isopropylsulfanylmethyl, methylsulfinylmethyl, trifluoromethylsulfinylmethyl, ethylsulfinylmethyl, 2,2,2- Trifluoroethylsulfinylmethyl, 2,2-difluoroethylsulfinylmethyl, isopropylsulfinylmethyl, methylsulfonylmethyl, trifluoromethylsulfonylmethyl, ethylsulfonylmethyl, 2,2,2-trifluoroethylsulfonylmethyl, 2,2-difluoroethylsulfonylmethyl, isopropylsulfonylmethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, methoxycarbonylethyl, ethoxycarbonylethyl, dimethylamino-carbonylmethyl, diethylaminocarbonylmethyl, N- ethyl N- methylaminocarbonylmethyl, N- isopropyl- N- methylaminocarbonylmethyl, dimethylaminocarbonylethyl, diethylaminocarbonylethyl, N Ethyl N- methylaminocarbonylethyl, N -Isopropyl- N -methylaminocarbonylethyl, N-cyclopropyl N- methylaminocarbonylmethyl, N -cyclopropyl N -methylaminocarbonylethyl, methylsulfanyl, trifluoromethylsulphanyl, ethylsulfanyl, 2,2,2-Trifluorethylsulfanyl, 2,2-Difluorethylsulfanyl , Isopropylsulfanyl, methylsulfinyl, trifluoromethylsulfinyl, ethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 2,2-difluoroethylsulfinyl, isopropylsulfinyl, methylsulfonyl, trifluoromethylsulfonyl, ethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 2,2-difluoroethylsulfonyl, isopropylsulfonyl, cyclopropyl, 1 Cyanocyclopropyl, 1-chlorocyclopropyl, 1-fluorocyclopropyl, 2-cyanocyclopropyl, 2-chlorocyclopropyl, 2-fluorocyclopropyl, 2,2,3,3-tetrafluorocyclopropyl, 2-cyclopropylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-trifluoromethylcyclohexyl, cyclopropylmethyl, cyclopropylethyl , Cyclobutylmethyl, morpholin-4-ylcarbonylmethyl, piperazin-1-ylcarbonylmethyl, 4-methylpiperazin-1-ylcarbonylmethyl, in each case optionally simple, trisubstituted or trisubstituted, identically or differently, by heterocyclylmethyl and heterocyclylethyl substituted by cyclopropyl, in each case by fluorine, chlorine, bromine, cyano, nitro, hydroxyl, amino, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, trifluoromethoxy, difluoromethoxy Heterocyclylmethyl and heterocyclylethyl, wherein the cyclopropyl radical optionally mono- or di-through Methyl, fluorine, chlorine, cyano or monosubstituted by cyclopropyl, optionally mono-, di- or trisubstituted by identical or different fluorine, chlorine, bromine, cyano, nitro, hydroxy, amino, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl , Difluoromethyl, methoxy, trifluoromethoxy, difluoromethoxy-substituted aryl, cyclopropyl-substituted aryl wherein the cyclopropyl radical is optionally mono- or di-substituted by methyl, fluoro, chloro, cyano or simply cyclopropyl, each optionally mono-, di- or tri-where the same or different Fluoro, chloro, bromo, cyano, nitro, hydroxy, amino, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, trifluoromethoxy, difluoromethoxy-substituted arylmethyl and arylethyl, cyclopropyl-substituted arylmethyl and arylethyl, where the cyclopropyl radical is optionally simple or twice by methyl, fluorine, chlorine, cyano or simply by cyclopropyl subst is hydrogenated, in each case optionally monosubstituted or disubstituted by identical or different, by hetarylmethyl and hetarylethyl substituted by fluorine, chlorine, bromine, cyano, nitro, hydroxyl, amino, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, trifluoromethoxy, difluoromethoxy cyclopropyl-substituted hetarylmethyl and hetarylethyl, where the cyclopropyl radical is optionally monosubstituted or disubstituted by methyl, fluorine, chlorine, cyano or simply by cyclopropyl, and in the case where R 2 is c), d) or g),
R 22
for a D radical from the series (D-1) to (D-3)
Figure imgb0233
 wherein
X 1
a radical selected from the group consisting of hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy and trifluoromethoxy,
R
for NR 18 R 19 or for any given mono-, di-, tri-, tetra- or quintuply fluorine, chlorine or mono- or di-cyano-substituted radical from the series C 1 -C 4 -alkyl, C 3 -C 4 -alkenyl, C 3 -C 4 -alkynyl, C 1 -C 2 -alkoxy-C 1 -C 2 -alkyl and C 1 -C 2 -alkyl-SC 1 -C 2 -alkyl, C 1 -C 2 -alkyl-S ( O) -C 1 -C 2 -alkyl, C 1 -C 2 -alkyl-S (O) 2 -C 1 -C 2 -alkyl, for R 18 -CO-C 1 -C 2 -alkyl, for NR 18 R 19 is -CO-C 1 -C 2 -alkyl, optionally optionally mono- or disubstituted by C 1 -C 2 -alkyl, C 1 -C 2 -alkoxy or C 1 -C 2 -haloalkyl or by an oxygen atom (leads to C = O) substituted C 3 -C 6 -cycloalkyl, optionally optionally mono- or disubstituted by C 1 -C 2 -alkyl, C 1 -C 2 -alkoxy or C 1 -C 2 -haloalkyl or C 3 -C 6 -cycloalkenyl which is substituted by an oxygen atom (leads to C = O) and is optionally mono- to disubstituted by C 1 -C 2 -alkyl, C 1 -C 2 -alkoxy or C 1 -C 2 -haloalkyl-substituted C 3 -C 6 -cycloalkyl-C 1 -C 2 alkyl, mono- or di-optionally substituted by C 1 -C 2 alkyl, C 1 -C 2 alkoxy or C 1 -C 2 -Haloalkyl-substituted C 3 -C 6 -cycloalkenyl-C 1 -C 2 -alkyl, heterocyclyl which is optionally monosubstituted or disubstituted by C 1 -C 2 -alkyl, C 1 -C 2 -alkoxy or C 1 -C 2 -haloalkyl , optionally mono- or disubstituted by C 1 -C 2 alkyl, C 1 -C 2 alkoxy or C 1 -C 2 -haloalkyl substituted heterocyclyl-C 1 -C 2 -alkyl or represents in each case optionally mono- or disubstituted by fluorine, Chlorine, bromine, cyano, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy-substituted phenyl, benzyl, pyridyl, pyrimidyl, thiazolyl, oxazolyl, pyrazolyl, Th ienyl, furanyl, pyridinylmethyl or thiazolylmethyl,
W
is a radical from the series S, SO and SO 2 ,
Y 3
a radical selected from the group consisting of hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy and trifluoromethoxy,
R 22
furthermore for one of the following E radicals
Figure imgb0234
Figure imgb0235
Figure imgb0236
Figure imgb0237
Figure imgb0238
 or in case R 2 = d),
R 22
also for the rest (E-13)
Figure imgb0239
 stands,
R 18
a radical selected from the group consisting of hydrogen, hydroxyl, in each case optionally mono-, di-, tri-, tetra- or trisubstituted by fluorine, chlorine or mono- or di-cyano-substituted C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkyl-C 1 -C 2 -alkyl, C 1 -C 4 -alkyl-S (O) -C 1 -C 2 - alkyl, C 1 -C 4 -alkyl-S (O) 2 -C 1 -C 2 -alkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 3 -alkyl, heterocyclyl and heterocyclyl-C 1 -C 3 -alkyl and in each case optionally mono- to trisubstituted by C 1 -C 4 -alkyl, C 1 -C 3 -haloalkyl, C 1 C 3 alkoxy, C 1 -C 3 haloalkoxy, cyclopropyl, fluorine, chlorine, bromine or cyano substituted phenyl, benzyl, pyridyl, pyrimidyl, thiazolyl, oxazolyl, pyrazolyl, thienyl, furanyl, pyridinylmethyl and thiazolylmethyl,
R 19
is hydrogen, an alkali or alkaline earth metal ion, an optionally mono- to quadruple C 1 -C 4 alkyl-substituted ammonium ion or each optionally optionally mono-, di-, tri-, tetra- or trisubstituted by fluorine, chlorine or mono- or disubstituted cyano Radical from the series C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl and C 1 -C 4 -alkyl-SC 1 -C 2 - alkyl, C 1 -C 4 -alkyl-S (O) -C 1 -C 2 -alkyl and C 1 -C 4 -alkyl-S (O) 2 -C 1 -C 2 -alkyl,
R 23
a radical selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 1 -C 6 alkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy, C 3 -C 6 cycloalkyloxy, C 1 -C 4 alkylthio-C 1 -C 4 alkyl, C 2 -C 4- alkenylthio-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl,
or, for R 2 = g),
R 22 and R 23
also together with the nitrogen atom to which they are attached are pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, thiomorpholinyl-1-oxide, thiomorpholinyl-1,1-dioxide, piperazinyl, 1-methylpiperazinyl or 2-oxo-1-methylpiperazinyl,
R 26
a radical selected from the group consisting of hydrogen, methyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, propenyl, propargyl, cyclopropyl, cyclopropylmethyl, methoxymethyl, methylsulfanyl, trifluoromethylsulfanyl, ethylsulfanyl, trifluoroethylsulfanyl, methylsulfinyl, trifluoromethylsulfinyl, ethylsulfinyl, trifluoroethylsulfinyl, methylthioethyl , Methylsulfinylethyl, methylsulfonylethyl and cyanomethyl and
R 27
is a radical selected from the group consisting of hydrogen, methyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, propenyl, propargyl, cyclopropyl, cyclopropylmethyl, methoxymethyl, methylthioethyl, methylsulfinylethyl, methylsulfonylethyl and cyanomethyl.

Vorzugsbereich (4): Eine hevorgehobene Gruppe von Verbindungen der Formel (I) sind solche, in welchen

A
für den A-Rest (A-a)
Figure imgb0240
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet,
G1
für C-B1 steht,
B1
für Wasserstoff steht,
B2
für Wasserstoff steht,
T
für ein Elektronenpaar steht,
R1
für Wasserstoff steht,
R2
a) für einen der folgenden Reste
Figure imgb0241
Figure imgb0242
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder
R2
c) für einen Rest der Formel
Figure imgb0243
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder
R2
d) für einen Rest der Formel
Figure imgb0244
 steht, worin die gestrichelte Linie die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, oder
R2
f) für C1-C6-Halogenalkyl steht, oder
R2
g) für einen Rest der Formel
Figure imgb0245
 steht, worin die gestrichelte Linie jeweils die Bindung zum Kohlenstoffatom des Bicyclus der Formel (I) bedeutet, worin
G2
für einen Rest aus der Reihe Wasserstoff, C1-C4-Alkyl und Halogen-C1-C4-alkyl steht,
R22
im Fall, dass R2 für g) steht, für einen Rest aus der Reihe Methyl, Ethyl, Isopropyl, n-Propyl, n-Butyl, iso-Butyl, sec-Butyl, tert-Butyl, 2,2,2-Trifluorethyl, 2,2-Difluorethyl, 2,2-Difluor-n-propyl, Methylsulfanyl-methyl, Methylsulfanylethyl, Methylsulfanyl-n-propyl, Methylsulfonyl, Ethylsulfonyl, Methylsulfonylmethyl, Ethylsulfonylmethyl, Isopropylsulfonylmethyl, Cyclopropyl steht, und im Fall, dass R2 für c), d) oder g) steht
R22
für (D-2)
Figure imgb0246
 steht, worin
X1
für einen Rest aus der Reihe Wasserstoff, Fluor, Chlor und Brom steht,
R
für gegebenfalls einfach, zweifach, dreifach, vierfach oder fünffach durch Fluor, Chlor substituiertes C1-C4-Alkyl steht,
W
für einen Rest aus der Reihe S, SO und SO2 steht,
Y3
für Wasserstoff oder Methyl steht und
R23
für Wasserstoff oder C1-C6-Alkyl steht oder im Fall, dass R2 für g) steht,
R22 und R23
gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, für Pyrrolidinyl oder Morpholinyl stehen.
Preferred Range (4): A preferred group of compounds of the formula (I) are those in which
A
for the A-residue (Aa)
Figure imgb0240
 in which the dashed line denotes the bond to the carbon atom of the bicyclic compound of the formula (I),
G 1
stands for CB 1 ,
B 1
stands for hydrogen,
B 2
stands for hydrogen,
T
stands for a pair of electrons,
R 1
stands for hydrogen,
R 2
a) for one of the following radicals
Figure imgb0241
Figure imgb0242
 wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R 2
c) a radical of the formula
Figure imgb0243
 wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R 2
d) for a radical of the formula
Figure imgb0244
 wherein the dashed line represents the bond to the carbon atom of the bicycle of formula (I), or
R 2
f) is C 1 -C 6 -haloalkyl, or
R 2
g) for a radical of the formula
Figure imgb0245
 in which the dashed line in each case denotes the bond to the carbon atom of the bicyclic compound of the formula (I) in which
G 2
a radical selected from the group consisting of hydrogen, C 1 -C 4 -alkyl and halogeno-C 1 -C 4 -alkyl,
R 22
in the case where R 2 is g), a radical selected from the group consisting of methyl, ethyl, isopropyl, n-propyl, n-butyl, isobutyl, sec-butyl, tert -butyl, 2,2,2-trifluoroethyl , 2,2-difluoroethyl, 2,2-difluoro-n-propyl, methylsulfanylmethyl, methylsulfanylethyl, methylsulfanyl-n-propyl, methylsulfonyl, ethylsulfonyl, methylsulfonylmethyl, ethylsulfonylmethyl, isopropylsulfonylmethyl, cyclopropyl, and when R 2 is c), d) or g)
R 22
for (D-2)
Figure imgb0246
 stands in which
X 1
is a radical from the series hydrogen, fluorine, chlorine and bromine,
R
optionally C 1 -C 4 -alkyl which is monosubstituted, disubstituted, trisubstituted, tetrasubstituted or pentavalent by fluorine, chlorine,
W
is a radical from the series S, SO and SO 2 ,
Y 3
is hydrogen or methyl and
R 23
is hydrogen or C 1 -C 6 -alkyl or, in the case where R 2 is g),
R 22 and R 23
together with the nitrogen atom to which they are attached represent pyrrolidinyl or morpholinyl.

Wenn in obigen Definitionen in Ringen Schwefel und/oder Stickstoff vorkommen, wie beispielsweise in Ausdrücken wie "in welchen die Ringe mindestens ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoff- und Schwefelatome nicht unmittelbar benachbart sein dürfen) und Stickstoff enthalten können" oder "in welchen ein oder zwei Ringglieder jeweils durch ein Heteroatom aus der Reihe Schwefel, Sauerstoff (wobei Sauerstoffatome nicht unmittelbar benachbart sein dürfen) und Stickstoff ersetzt sein können", dann kann, sofern nichts anderes angegeben ist, der Schwefel auch als SO oder SO2 vorliegen, der Stickstoff, sofern er nicht als -N= vorliegt, neben NH auch als N-Alkyl (insbesondere N-C1-C6-Alkyl) vorliegen.When in the above definitions in rings sulfur and / or nitrogen occur, as for example in terms such as "in which the rings at least one heteroatom from the series sulfur, oxygen (oxygen atoms and sulfur atoms may not be immediately adjacent) and nitrogen may contain" or "in which one or two ring members may each be replaced by a heteroatom selected from sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen", then, unless otherwise stated, the sulfur may also be referred to as SO or SO 2 are present, the nitrogen, if it is not present as -N =, in addition to NH also as N-alkyl (especially NC 1 -C 6 alkyl).

In den bevorzugten Definitionen, deren Kombination den Vorzugsbereich (1) bildet, ist, sofern nichts anderes angegeben ist,
Kation ein Alkaliion ausgewählt aus der Reihe Lithium, Natrium, Kalium, Rubidium, Cäsium, bevorzugt aus der Reihe Lithium, Natrium, Kalium oder ein
Erdalkaliion ausgewählt aus der Reihe Beryllium, Magnesium, Calcium, Strontium, Barium, bevorzugt aus der Reihe Magnesium, Calcium,
Halogen ausgewählt aus der Reihe Fluor, Chlor, Brom und Iod, bevorzugt wiederum aus der Reihe Fluor, Chlor und Brom,
Aryl (auch als Teil einer größeren Einheit, wie beispielsweise Arylalkyl) ausgewählt aus der Reihe Phenyl, Naphthyl, Anthryl, Phenanthrenyl und steht wiederum bevorzugt für Phenyl,
Hetaryl (gleichbedeutend mit Heteroaryl, auch als Teil einer größeren Einheit, wie beispielsweise Hetarylalkyl) ausgewählt aus der Reihe Furyl, Thienyl, Pyrrolyl, Pyrazolyl, Imidazolyl, 1,2,3-Triazolyl, 1,2,4-Triazolyl, Oxazolyl, Isoxazolyl, Thiazolyl, Isothiazolyl, 1,2,3-Oxadiazolyl, 1,2,4-Oxadiazolyl, 1,3,4-Oxadiazolyl, 1,2,5-Oxadiazolyl, 1,2,3-Thiadiazolyl, 1,2,4-Thiadiazolyl, 1,3,4-Thiadiazolyl, 1,2,5-Thiadiazolyl, Pyridyl, Pyrimidinyl, Pyridazinyl, Pyrazinyl, 1,2,3-Triazinyl, 1,2,4-Triazinyl, 1,3,5-Triazinyl, Benzofuryl, Benzisofuryl, Benzothienyl, Benzisothienyl, Indolyl, Isoindolyl, Indazolyl, Benzothiazolyl, Benzisothiazolyl, Benzoxazolyl, Benzisoxazolyl, Benzimidazolyl, 2,1,3-Benzoxadiazole, Chinolinyl, Isochinolinyl, Cinnolinyl, Phthalazinyl, Chinazolinyl, Chinoxalinyl, Naphthyridinyl, Benzotriazinyl, Purinyl, Pteridinyl und Indolizinyl,
Heterocyclyl ein gesättigter 4-, 5- oder 6-Ring, der 1 oder 2 Stickstoffatome und/oder ein Sauerstoffatom und/oder ein Schwefelatom enthält, beispielsweise Azetidinyl, Azolidinyl, Azinanyl, Oxetanyl, Oxolanyl, Oxanyl, Dioxanyl, Thiethanyl, Thiolanyl, Thianyl, Tetrahydrofuryl, Piperazinyl, Morpholinyl.
In den besonders bevorzugten Definitionen, deren Kombination den Vorzugsbereich (2) bildet, ist, sofern nichts anderes angegeben ist,
Kation für ein Alkaliion ausgewählt aus der Reihe Lithium, Natrium, Kalium, Rubidium, Cäsium, bevorzugt aus der Reihe Lithium, Natrium, Kalium oder ein
Erdalkaliion ausgewählt aus der Reihe Beryllium, Magnesium, Calcium, Strontium, Barium, bevorzugt aus der Reihe Magnesium, Calcium,
Halogen ausgewählt aus der Reihe Fluor, Chlor, Brom und Iod, bevorzugt wiederum aus der Reihe Fluor, Chlor und Brom,
Aryl (auch als Teil einer größeren Einheit, wie beispielsweise Arylalkyl) ausgewählt aus der Reihe Phenyl, Naphthyl, Anthryl, Phenanthrenyl und steht wiederum bevorzugt für Phenyl,
Hetaryl (gleichbedeutend mit Heteroaryl, auch als Teil einer größeren Einheit, wie beispielsweise Hetarylalkyl) ausgewählt aus der Reihe Pyrazolyl, Imidazolyl, 1,2,3-Triazolyl, 1,2,4-Triazolyl, Oxazolyl, Isoxazolyl, Thiazolyl, Isothiazolyl, Pyridyl, Pyrimidinyl, Pyridazinyl, Pyrazinyl, 1,2,3-Triazinyl, 1,2,4-Triazinyl, 1,3,5-Triazinyl,
Heterocyclyl ausgewählt aus der Reihe Azetidinyl, Azolidinyl, Azinanyl, Oxetanyl, Oxolanyl, Oxanyl, Dioxanyl, Thiethanyl, Thiolanyl, Thianyl, Tetrahydrofuryl, Piperazinyl, Morpholinyl.In the preferred definitions, the combination of which forms the preferred range (1), unless otherwise specified
Cation an alkali metal ion selected from the series lithium, sodium, potassium, rubidium, cesium, preferably from the series lithium, sodium, potassium or a
Alkaline earth ion selected from the series beryllium, magnesium, calcium, strontium, barium, preferably from the series magnesium, calcium,
Halogen selected from the group fluorine, chlorine, bromine and iodine, preferably again from the series fluorine, chlorine and bromine,
Aryl (also as part of a larger unit, such as, for example, arylalkyl) selected from the group consisting of phenyl, naphthyl, anthryl, phenanthrenyl and in turn preferably represents phenyl,
Hetaryl (equivalent to heteroaryl, also as part of a larger moiety such as hetarylalkyl) selected from the series furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl , Thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4 Thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl , Benzofuryl, benzisofuryl, benzothienyl, benzisothienyl, indolyl, isoindolyl, indazolyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, benzimidazolyl, 2,1,3-benzoxadiazoles, quinolinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, benzotriazinyl, purinyl , Pteridinyl and indolizinyl,
Heterocyclyl a saturated 4-, 5- or 6-membered ring containing 1 or 2 nitrogen atoms and / or an oxygen atom and / or a sulfur atom, for example azetidinyl, azolidinyl, azinanyl, oxetanyl, oxolanyl, oxanyl, dioxanyl, thiethanyl, thiolanyl, thianyl , Tetrahydrofuryl, piperazinyl, morpholinyl.
In the particularly preferred definitions, the combination of which forms the preferred range (2), unless otherwise stated,
Cation for an alkali ion selected from the series lithium, sodium, potassium, rubidium, cesium, preferably from the series lithium, sodium, potassium or a
Alkaline earth ion selected from the series beryllium, magnesium, calcium, strontium, barium, preferably from the series magnesium, calcium,
Halogen selected from the group fluorine, chlorine, bromine and iodine, preferably again from the series fluorine, chlorine and bromine,
Aryl (also as part of a larger unit, such as, for example, arylalkyl) selected from the group consisting of phenyl, naphthyl, anthryl, phenanthrenyl and in turn preferably represents phenyl,
Hetaryl (equivalent to heteroaryl, also as part of a larger unit, such as hetarylalkyl) selected from the series pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyridyl , Pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl,
Heterocyclyl selected from azetidinyl, azolidinyl, azinanyl, oxetanyl, oxolanyl, oxanyl, dioxanyl, thiethanyl, thiolanyl, thianyl, tetrahydrofuryl, piperazinyl, morpholinyl.

In den ganz besonders bevorzugten Definitionen bzw. den insbesondere bevorzugten Definitionen, deren Kombination den Vorzugsbereich (3) bilden, steht, sofern nichts anderes angegeben ist,
Kation für ein Alkaliion aus der Reihe Lithium, Natrium, Kalium, Rubidium, Cäsium, bevorzugt aus der Reihe Lithium, Natrium, Kalium oder ein
Erdalkaliion aus der Reihe Beryllium, Magnesium, Calcium, Strontium, Barium, bevorzugt aus der Reihe Magnesium, Calcium,
Heterocyclyl für Oxetanyl, Thiethanyl, Tetrahydrofuryl und Morpholinyl.In the most particularly preferred definitions or the particularly preferred definitions whose combination form the preferred range (3), unless otherwise stated,
Cation for an alkali metal ion from the series lithium, sodium, potassium, rubidium, cesium, preferably from the series lithium, sodium, potassium or a
Beryllium, magnesium, calcium, strontium, barium alkaline earth metal, preferably magnesium, calcium,
Heterocyclyl for oxetanyl, thiethanyl, tetrahydrofuryl and morpholinyl.

Aryl für Phenyl,
Hetaryl (gleichbedeutend mit Heteroaryl, auch als Teil einer größeren Einheit, wie beispielsweise Hetarylalkyl) für einen Rest aus der Reihe Pyridyl, Pyrimidyl, Pyrazinyl, Pyridazinyl, Thiazolyl und Pyrazolyl.Aryl for phenyl,
Hetaryl (synonymous with heteroaryl, as part of a larger unit, such as hetarylalkyl) for a radical from the series pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, thiazolyl and pyrazolyl.

In den Definitionen, die den Vorzugsbereich (4) bilden, steht
Halogen für Fluor, Chlor, Brom und Iod, bevorzugt wiederum für Fluor, Chlor und Brom.In the definitions that make up the preferential range (4) stands
Halogen for fluorine, chlorine, bromine and iodine, preferably again fluorine, chlorine and bromine.

Durch Halogen substituierte Reste, z.B. Halogenalkyl (= Haloalkyl), sind einfach oder mehrfach bis zur maximal möglichen Substituentenzahl halogeniert. Bei mehrfacher Halogenierung können die Halogenatome gleich oder verschieden sein. Halogen steht dabei für Fluor, Chlor, Brom oder Iod, insbesondere für Fluor, Chlor oder Brom.Halo-substituted radicals, for example haloalkyl (= haloalkyl), are halogenated once or several times up to the maximum possible number of substituents. With multiple halogenation, the halogen atoms be the same or different. Halogen is fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine or bromine.

Gesättigte oder ungesättigte Kohlenwasserstoffreste wie Alkyl oder Alkenyl können, auch in Verbindung mit Heteroatomen, wie z.B. in Alkoxy, soweit möglich, jeweils geradkettig oder verzweigt sein.Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl, may also be used in conjunction with heteroatoms, e.g. in alkoxy, as far as possible, in each case straight-chain or branched.

Gegebenenfalls substituierte Reste können, wenn nichts anderes erwähnt ist, einfach oder mehrfach substituiert sein, wobei bei Mehrfachsubstitutionen die Substituenten gleich oder verschieden sein können.Unless otherwise specified, optionally substituted radicals may be monosubstituted or polysubstituted, with multiple substituents the substituents being the same or different.

Wenn T im Rest A der Formel (A-a)

Figure imgb0247
für ein Elektronenpaar steht, liegt der Rest als Pyridinderivat der Formel
Figure imgb0248
 vor.When T in the radical A of the formula (Aa)
Figure imgb0247
 represents an electron pair, the remainder is a pyridine derivative of the formula
Figure imgb0248
 in front.

Wenn T im Rest A der Formel (A-a)

Figure imgb0249
für Sauerstoff steht, liegt der Rest als Pyridin-N-Oxid-derivat der Formel
Figure imgb0250
 vor. Auf die Darstellung der Formalladungen (+ am Stickstoff und - am Sauerstoff) wurde hier verzichtet.When T in the radical A of the formula (Aa)
Figure imgb0249
 is oxygen, the remainder is pyridine N -oxide derivative of the formula
Figure imgb0250
 in front. The representation of the formal charges (+ on the nitrogen and - on the oxygen) was omitted here.

Die oben aufgeführten allgemeinen oder in Vorzugsbereichen aufgeführten Restedefinitionen bzw. Erläuterungen gelten für die Endprodukte und für die Ausgangsprodukte und Zwischenprodukte entsprechend. Diese Restedefinitionen können untereinander, also auch zwischen den jeweiligen Vorzugsbereichen, beliebig kombiniert werden.The general or preferred radical definitions or explanations given above apply correspondingly to the end products and to the starting materials and intermediates. These remainder definitions can be combined with one another as desired, ie also between the respective preferred ranges.

Erfindungsgemäß bevorzugt sind Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als bevorzugt aufgeführten Bedeutungen vorliegt (Vorzugsbereich (1)).Preference according to the invention is given to compounds of the formula (I) which contain a combination of the meanings listed above as being preferred (preferred range (1)).

Erfindungsgemäß besonders bevorzugt sind Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als besonders bevorzugt aufgeführten Bedeutungen vorliegt (Vorzugsbereich (2)).Particular preference according to the invention is given to compounds of the formula (I) which contain a combination of the meanings listed above as being particularly preferred (preferred range (2)).

Erfindungsgemäß ganz besonders bevorzugt sind Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als ganz besonders bevorzugt aufgeführten Bedeutungen vorliegt (Vorzugsbereich (3)).Very particular preference according to the invention is given to compounds of the formula (I) which contain a combination of the meanings listed above as being very particularly preferred (preferred range (3)).

Erfindungsgemäß insbesonders bevorzugt sind Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als hervorgehoben aufgeführten Bedeutungen vorliegt (Vorzugsbereich (4)).Particular preference according to the invention is given to compounds of the formula (I) which contain a combination of the meanings listed above as being highlighted (preferred range (4)).

Eine bevorzugte Ausführungsform der Erfindung betrifft Verbindungen der Formel (I), in welchen A für den Rest der Formel (A-a)

Figure imgb0251
steht.A preferred embodiment of the invention relates to compounds of the formula (I) in which A represents the radical of the formula (Aa)
Figure imgb0251
 stands.

Eine weitere bevorzugte Ausführungsform der Erfindung betrifft Verbindungen der Formel (I), in welchen A für Pyridin-3-yl steht.A further preferred embodiment of the invention relates to compounds of the formula (I) in which A is pyridin-3-yl.

Eine weitere bevorzugte Ausführungsform der Erfindung betrifft Verbindungen der Formel (I), in welchen A für 5-Fluor-pyridin-3-yl steht.A further preferred embodiment of the invention relates to compounds of the formula (I) in which A is 5-fluoropyridin-3-yl.

Eine weitere bevorzugte Ausführungsform der Erfindung betrifft Verbindungen der Formel (I), in welchen A für Pyrimidin-5-yl steht.A further preferred embodiment of the invention relates to compounds of the formula (I) in which A is pyrimidin-5-yl.

Eine weitere bevorzugte Ausführungsform der Erfindung betrifft Verbindungen der Formel (I), in welchen A für Pyridazin-4-yl steht.A further preferred embodiment of the invention relates to compounds of the formula (I) in which A is pyridazin-4-yl.

Eine weitere bevorzugte Ausführungsform der Erfindung betrifft Verbindungen der Formel (I), in welchen R2 für die unter a) genannten Reste steht.A further preferred embodiment of the invention relates to compounds of the formula (I) in which R 2 represents the radicals mentioned under a).

Eine weitere bevorzugte Ausführungsform der Erfindung betrifft Verbindungen der Formel (I), in welchen R2 für die unter b) genannten Reste steht.A further preferred embodiment of the invention relates to compounds of the formula (I) in which R 2 represents the radicals mentioned under b).

Eine weitere bevorzugte Ausführungsform der Erfindung betrifft Verbindungen der Formel (I), in welchen R2 für die unter c) genannten Reste steht.A further preferred embodiment of the invention relates to compounds of the formula (I) in which R 2 represents the radicals mentioned under c).

Eine weitere bevorzugte Ausführungsform der Erfindung betrifft Verbindungen der Formel (I), in welchen R2 für die unter d) genannten Reste steht.A further preferred embodiment of the invention relates to compounds of the formula (I) in which R 2 represents the radicals mentioned under d).

Eine weitere bevorzugte Ausführungsform der Erfindung betrifft Verbindungen der Formel (I), in welchen R2 für die unter e) genannten Reste steht.A further preferred embodiment of the invention relates to compounds of the formula (I) in which R 2 is the radical mentioned under e).

Eine weitere bevorzugte Ausführungsform der Erfindung betrifft Verbindungen der Formel (I), in welchen R2 für die unter f) genannten Reste steht.A further preferred embodiment of the invention relates to compounds of the formula (I) in which R 2 is the radical mentioned under f).

Eine weitere bevorzugte Ausführungsform der Erfindung betrifft Verbindungen der Formel (I), in welchen R2 für die unter g) genannten Reste steht.A further preferred embodiment of the invention relates to compounds of the formula (I) in which R 2 is the radical mentioned under g).

Eine weitere bevorzugte Ausführungsform der Erfindung betrifft Verbindungen der Formel (I), in welchen R2 für den Rest (D-2)

Figure imgb0252
steht.A further preferred embodiment of the invention relates to compounds of the formula (I) in which R 2 is the radical (D-2)
Figure imgb0252
 stands.

Die oben aufgeführten allgemeinen oder in Vorzugsbereichen aufgeführten Restedefinitionen bzw. Erläuterungen gelten für die Endprodukte (auch für die Verbindungen der später aufgeführten Formeln (I-A) bis (I-N)) und für die Ausgangsprodukte und Zwischenprodukte entsprechend. Diese Restedefinitionen können untereinander, also auch zwischen den jeweiligen Vorzugsbereichen, beliebig kombiniert werden.The general or preferred radical definitions or explanations given above apply to the end products (also for the compounds of the formulas (I-A) to (I-N) listed below) and correspondingly to the starting materials and intermediates. These remainder definitions can be combined with one another as desired, ie also between the respective preferred ranges.

In einer bevorzugten Ausführungsform betrifft die Erfindung Verbindungen der Formel (I-A)

Figure imgb0253
In a preferred embodiment, the invention relates to compounds of the formula (IA)
Figure imgb0253

In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung Verbindungen der Formel (I-B)

Figure imgb0254
In a further preferred embodiment, the invention relates to compounds of the formula (IB)
Figure imgb0254

In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung Verbindungen der Formel (I-C)

Figure imgb0255
In a further preferred embodiment, the invention relates to compounds of the formula (IC)
Figure imgb0255

In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung Verbindungen der Formel (I-D)

Figure imgb0256
In a further preferred embodiment, the invention relates to compounds of the formula (ID)
Figure imgb0256

In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung Verbindungen der Formel (I-E)

Figure imgb0257
In a further preferred embodiment, the invention relates to compounds of the formula (IE)
Figure imgb0257

In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung Verbindungen der Formel (I-F)

Figure imgb0258
In a further preferred embodiment, the invention relates to compounds of the formula (IF)
Figure imgb0258

In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung Verbindungen der Formel (I-G)

Figure imgb0259
In a further preferred embodiment, the invention relates to compounds of the formula (IG)
Figure imgb0259

In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung Verbindungen der Formel (I-H)

Figure imgb0260
In a further preferred embodiment, the invention relates to compounds of the formula (IH)
Figure imgb0260

In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung Verbindungen der Formel (I-I)

Figure imgb0261
In a further preferred embodiment, the invention relates to compounds of the formula (II)
Figure imgb0261

In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung Verbindungen der Formel (I-J)

Figure imgb0262
In a further preferred embodiment, the invention relates to compounds of the formula (IJ)
Figure imgb0262

In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung Verbindungen der Formel (I-K)

Figure imgb0263
In a further preferred embodiment, the invention relates to compounds of the formula (IK)
Figure imgb0263

In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung Verbindungen der Formel (I-L)

Figure imgb0264
In a further preferred embodiment, the invention relates to compounds of the formula (II)
Figure imgb0264

In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung Verbindungen der Formel (I-M)

Figure imgb0265
In a further preferred embodiment, the invention relates to compounds of the formula (III)
Figure imgb0265

In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung Verbindungen der Formel (I-N)

Figure imgb0266
In a further preferred embodiment, the invention relates to compounds of the formula (IN)
Figure imgb0266

In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung Verbindungen der Formel (I-O)

Figure imgb0267
In a further preferred embodiment, the invention relates to compounds of the formula (IO)
Figure imgb0267

In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung Verbindungen der Formel (I-P)

Figure imgb0268
In a further preferred embodiment, the invention relates to compounds of the formula (IP)
Figure imgb0268

In den Formeln (I-A) bis (I-P) haben die Variablen die weiter oben genannten Bedeutungen.In the formulas (I-A) to (I-P), the variables have the meanings mentioned above.

Die Verbindungen der Formel (I) und deren Säureadditionssalze und Metallsalzkomplexe besitzen gute Wirksamkeit, insbesondere zur Bekämpfung von tierischen Schädlingen, zu denen Arthropoden und insbesondere Insekten zählen.The compounds of the formula (I) and their acid addition salts and metal salt complexes have good activity, in particular for combating animal pests, which include arthropods and in particular insects.

Als geeignete Salze der Verbindungen der Formel (I) können übliche nicht toxische Salze, d. h. Salze mit entsprechenden Basen und Salze mit zugesetzten Säuren genannt werden. Vorzugsweise sind Salze mit anorganischen Basen, wie Alkalimetallsalze, beispielsweise Natrium-, Kalium- oder Cäsiumsalze, Erdalkalimetallsalze, beispielsweise Calcium- oder Magnesiumsalze, Ammoniumsalze, Salze mit organischen Basen sowie mit anorganischen Aminen, beispielsweise Triethylammonium-, Dicyclohexylammonium-, N,N'-Dibenzylethylendiammonium-, Pyridinium-, Picolinium- oder Ethanolammoniumsalze, Salze mit anorganischen Säuren, beispielsweise Hydrochloride, Hydrobromide, Dihydrosulfate, Trihydrosulfate, oder Phosphate, Salze mit organischen Carbonsäuren oder organischen Sulfosäure, beispielsweise Formiate, Acetate, Trifluoracetate, Maleate, Tartrate, Methansulfonate, Benzolsulfonate oder para-Toluolsulfonate, Salze mit basischen Aminosäuren, beispielsweise Arginate, Aspartate oder Glutamate und Ähnliches zu nennen.Suitable salts of the compounds of the formula (I) may be customary non-toxic salts, ie salts with corresponding bases and salts with added acids. Preferably, salts with inorganic bases, such as alkali metal salts, for example sodium, potassium or cesium salts, alkaline earth metal salts, for example calcium or magnesium salts, ammonium salts, salts with organic bases and with inorganic amines, for example triethylammonium, Dicyclohexylammonium-, N, N '- Dibenzylethylenediammonium, pyridinium, picolinium or ethanolammonium salts, salts with inorganic acids, for example hydrochlorides, hydrobromides, dihydrosulfates, trihydrosulfates, or phosphates, salts with organic carboxylic acids or organic sulfonic acid, for example formates, acetates, trifluoroacetates, maleates, tartrates, methanesulfonates, benzenesulfonates or para- toluenesulfonates, salts with basic amino acids, for example, arginates, aspartates or glutamates, and the like.

Die Verbindungen der Formel (I) können gegebenenfalls auch in Abhängigkeit von der Art der Substituenten als Stereoisomere, d.h. als geometrische und/oder als optische Isomere oder Isomerengemische vorliegen in unterschiedlichen Zusammensetzungen vorliegen. Sowohl die reinen Stereoisomeren als auch beliebige Gemische dieser Isomeren sind Gegenstand dieser Erfindung, auch wenn hier im Allgemeinen nur von Verbindungen der Formel (I) die Rede ist.Depending on the nature of the substituents, the compounds of the formula (I) may also be present in different compositions as stereoisomers, ie as geometric and / or optical isomers or mixtures of isomers. Both the pure Stereoisomers as well as any mixtures of these isomers are the subject of this invention, although in general only compounds of the formula (I) are mentioned here.

Die Erfindung betrifft daher sowohl die reinen Enantiomeren und Diastereomeren, als auch deren Gemische zur Bekämpfung von tierischen Schädlingen, zu denen Arthropoden und insbesondere Insekten zählen.The invention therefore relates to both the pure enantiomers and diastereomers, as well as their mixtures for controlling animal pests, which include arthropods and in particular insects.

Vorzugsweise werden erfindungsgemäß jedoch die optisch aktiven, stereoisomeren Formen der Verbindungen der Formel (I) und deren Salze verwendet.However, the optically active, stereoisomeric forms of the compounds of the formula (I) and salts thereof are preferably used according to the invention.

Weiter wurde gefunden, dass sich die neuen Verbindungen der Formel (I) und auch diejenigen in der Tabelle 1 aufgeführten Verbindungen, die nicht unter die Formel (I) fallen, nach den im Folgenden beschriebenen Verfahren herstellen lassen.It has furthermore been found that the novel compounds of the formula (I) and also those compounds listed in Table 1 which do not fall under the formula (I) can be prepared by the processes described below.

Verbindungen der Formel (I), in denen der Heterocyclus A für gegegebenenfalls mit einem Rest B2 substituiertes Pyrimdin-5-yl (A-a; G1 = N), Pyridin-3-yl (A-a; G1 = C-B1), Pyrazin-2-yl (A-b), Pyridazin-3-yl (A-c), Thiazol-5-yl (A-d), Isothiazol-4-yl (A-e) und Pyrazol-4-yl (A-f) steht, können beispielsweise gemäß Reaktionsschema I in zwei oder drei Schritten hergestellt werden.Compounds of the formula (I) in which the heterocycle A is pyrimdin-5-yl optionally substituted by a radical B 2 (Aa; G 1 = N), pyridin-3-yl (Aa; G 1 = CB 1 ), pyrazine 2-yl (Ab), pyridazin-3-yl (Ac), thiazol-5-yl (Ad), isothiazol-4-yl (Ae) and pyrazol-4-yl (Af) can, for example, according to Reaction Scheme I be made in two or three steps.

Reaktionsschema I - Methode AScheme I - Method A

Figure imgb0269
Figure imgb0269

  • LG = Leaving group, z. B. Halogen, CO-OR (R = Aryl, Alkyl) N-lmidazol-1-yl, OH etc.LG = Leaving group, z. As halogen, CO-OR (R = aryl, alkyl) N-imidazol-1-yl, OH etc.
  • X = Halogen, z. B. Br oder ClX = halogen, e.g. B. Br or Cl

Im Reaktionsschema I haben A, R1 und R2 die oben genannten und gegebenenfalls weitere, für die Herstellverfahren relevante Bedeutungen, die aus dem Text bzw. dem Zusammenhang hervorgehen.In Reaction Scheme I, A, R 1 and R 2 have the abovementioned and, if appropriate, further meanings which are relevant for the preparation processes and which emerge from the text or the context.

Beispielsweise können die substituierten Aminopyridine der Formel (A-I) mit den entsprechenden aktivierten Carbonsäuren (z. B. als Carbonsäurechlorid oder dessen Hydrochlorid) der Formel (A-II) in Gegenwart von basischen Reaktionshilfsmitteln in einem ersten Reaktionsschritt zu Verbindungen der Formel (A-III) umgesetzt werden. Diese werden dann durch entsprechende Schwefeldonatoren wie z. B. Lawesson's Reagenz zu Verbindungen der Formel (A-IV) thioniert. Wird diese Reaktion bei erhöhter Temperatur durchgeführt, so können die entstehenden Thioamide der Formel (A-IV) direkt zu Verbindungen der Formel (I) cyclisieren. Andernfalls können Verbindungen der Formel (A-IV) in einem dritten Reaktionsschritt in Gegenwart einer geeigneten Base, beispielsweise Kaliumcarbonat, zu Verbindungen der Formel (I) cyclisiert werden.For example, the substituted aminopyridines of the formula (AI) can be reacted with the corresponding activated carboxylic acids (for example as the carboxylic acid chloride or its hydrochloride) of the formula (A-II) in the presence of basic reaction auxiliaries in a first reaction step to give compounds of the formula (A-III ) are implemented. These are then replaced by appropriate sulfur donors such. B. Lawesson's reagent to compounds of formula (A-IV) thioniert. If this reaction is carried out at elevated temperature, the resulting thioamides of the formula (A-IV) can be cyclized directly to give compounds of the formula (I). Otherwise, compounds of the formula (A-IV) can be cyclized in a third reaction step in the presence of a suitable base, for example potassium carbonate, to give compounds of the formula (I).

Methode A - Schritt 1: Die Verbindungen der Formel (A-I) sind teilweise bekannt und kommerziell erhältlich bzw. können nach im Prinzip bekannten Herstellungsverfahren (z. B. für R1 = H, R2 = Cl; 2,6-Dichlorpyridin-3-amin, vgl. WO 2007/015877 und WO 2014/02234 ) erhalten werden. Method A - Step 1: The compounds of the formula (AI) are known in some cases and are commercially available or can be prepared by methods known in principle (for example for R 1 = H, R 2 = Cl, 2,6-dichloropyridine-3 amine, cf. WO 2007/015877 and WO 2014/02234 ).

Die Verbindungen der Formel (A-II) sind teilweise bekannt und kommerziell erhältlich bzw. können nach im Prinzip bekannten Herstellungsverfahren (z. B. für A = Pyridin-3-yl, LG = Cl; Nicotinsäurechlorid ( Journal of the American Chemical Society (1953), 75, 4364 oder für A = 5-Fluorpyridin-3-yl, LG = Cl; 5-Fluornicotinoylchlorid ( US 2,516,830 )) erhalten werden.The compounds of the formula (A-II) are known in some cases and are commercially available or can be prepared by processes known in principle (for example for A = pyridin-3-yl, LG = Cl, nicotinic acid chloride (cf. Journal of the American Chemical Society (1953), 75, 4364 or for A = 5-fluoropyridin-3-yl, LG = Cl; 5-fluoronicotinoyl chloride ( US 2,516,830 )).

Für den Amidierungsschritt sind zahlreiche Reaktionsbedingungen beschrieben worden, z.B. G. Benz in Comprehensive Organic Synthesis, 1st Ed., Pergamon Press, Oxford, 1991, Vol. 6, S. 381-417 ; P.D. Bailey et al. in Comprehensive Organic Functional Group Transformation, 1st Ed., Elsevier Science Ltd., Oxford, 1995, Vol. 5, S. 257-308 und R.C. Larock in Comprehensive Organic Transformations, 2nd Ed., Wiley-VCH, New York, Weinheim, 1999, S. 1929-1994 . Einige dieser Reaktionen verlaufen über intermediäre Carbonsäurechloride, die isoliert oder in-situ aus A-II (LG = OH) erzeugt eingesetzt werden können.Numerous reaction conditions have been described for the amidation step, eg G. Benz in Comprehensive Organic Synthesis, 1st Ed., Pergamon Press, Oxford, 1991, Vol. 6, pp. 381-417 ; PD Bailey et al. in Comprehensive Organic Functional Group Transformation, 1st Ed., Elsevier Science Ltd., Oxford, 1995, Vol. 5, pp. 257-308 and RC Larock in Comprehensive Organic Transformations, 2nd ed., Wiley-VCH, New York, Weinheim, 1999, pp. 1929-1994 , Some of these reactions proceed via intermediate carboxylic acid chlorides, which can be used in isolation or generated in situ from A-II (LG = OH).

Die Amidierungsreaktionen erfolgen gegebenenfalls in Gegenwart eines Kondensationsmittels, gegebenenfalls in Gegenwart eines Säureakzeptors und gegebenenfalls in Gegenwart eines Lösungsmittels.Optionally, the amidation reactions are carried out in the presence of a condensing agent, optionally in the presence of an acid acceptor and optionally in the presence of a solvent.

Als Kondensationsmittel kommen alle üblicherweise für derartige Amidierungsreaktionen verwendbaren Kondensationsmittel infrage. Beispielhaft genannt seien Säurehalogenidbildner wie Phosgen, Phosphortrichlorid, Oxalylchlorid oder Thionylchlorid; Carbodiimide, wie N,N'-Dicyclohexylcarbodiimid (DCC) und 1-(3-Dimethylaminopropyl)-3-ethyl-carbodiimid (EDCI), oder andere übliche Kondensationsmittel, wie Phosphorpentoxid, Polyphosphorsäure, N,N'-Carbonyldiimidazol, 2-Chlorpyridin 1-Methoiodid (Mukaiyamas Reagenz), 2-Ethoxy-N-ethoxycarbonyl-1,2-dihydrochinolin (EEDQ), Triphenylphosphin/Tetrachlorkohlenstoff, Bromtripyrrolidino-phosphonium-hexafluorphosphat (BROP), O-(1H-Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium-hexafluorphosphat (BOP), N,N,N',N'-Bis(tetramethylen)cloruroniumtetrafluorborat, O-(1H-Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium-hexafluorphosphat (HBTU), O-(1H-Benzotriazol-1-yl)-N,N,N',N'-bis(tetramethylen)uronium-hexafluorphosphat, O-(1H-Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium-tetrafluorborat (TBTU), O-(1H-Benzotriazol-1-yl)-N,N,N',N'-bis(tetramethylen)uronium-tetrafluorborat, O-(7-Azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium-hexafluorphosphat (HATU), 1-Hydroxybenzotriazol (HOBt) und 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholiniumsalz (DMT.MM), meistens als Chlorid verfügbar. Diese Reagenzien können separat oder gegebenenfalls in Kombination eingesetzt werden.Suitable condensing agents are all condensing agents customarily used for such amidation reactions. Examples which may be mentioned are acid halide formers such as phosgene, phosphorus trichloride, oxalyl chloride or thionyl chloride; Carbodiimides such as N, N'- dicyclohexylcarbodiimide (DCC) and 1- (3-dimethylaminopropyl) -3-ethyl-carbodiimide (EDCI), or other conventional condensing agents such as phosphorus pentoxide, polyphosphoric acid, N, N'- carbonyldiimidazole, 2-chloropyridine 1-Methoiodide (Mukaiyamas reagent), 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ), triphenylphosphine / carbon tetrachloride, bromotripyrrolidino-phosphonium hexafluorophosphate (BROP), O- ( 1H- benzotriazol-1-yloxy) tris (dimethylamino) phosphonium hexafluorophosphate (BOP), N, N, N ', N' -bis (tetramethylene) cloruroniumtetrafluorborat, O- (1H-benzotriazol-1-yl) - N, N, N ', N' -tetramethyluronium- hexafluorophosphate (HBTU), O- ( 1H- benzotriazol-1-yl) -N , N, N ', N'-bis (tetramethylene) uronium hexafluorophosphate, O- ( 1H- benzotriazol-1-yl) -N , N , N ', N'-tetramethyluronium tetrafluoroborate (TBTU), O- ( 1H- benzotriazol-1-yl) -N , N, N', N'-bis (tetramethylene) uronium tetrafluoroborate, O- (7-azabenzotriazole -1-yl) - N, N, N ', N'- tetramethyluronium hexafluorophosphate (HATU), 1-hydroxybenzotriazole zol (HOBt) and 4- (4,6-dimethoxy-1,3,5-triazin-2-yl) -4-methylmorpholinium salt (DMT.MM), most commonly available as chloride. These reagents may be used separately or optionally in combination.

Als Säureakzeptor kommen alle üblichen anorganischen oder organischen Basen infrage, beispielsweise Triethylamin, Diisopropylethylamin, N-Methylmorpholin oder N,N-Dimethylaminopyridin. Das erfindungsgemäße Verfahren A (Schritt 1) wird gegebenenfalls in Gegenwart eines geeigneten Reaktionshilfstoffes wie beispielsweise N,N-Dimethylformamid oder N,N-Dimethylaminopyridin durchgeführt.Suitable acid acceptors are all customary inorganic or organic bases, for example triethylamine, diisopropylethylamine, N- methylmorpholine or N, N- dimethylaminopyridine. If appropriate, process A according to the invention (step 1) is carried out in the presence of a suitable reaction auxiliary, for example N, N- dimethylformamide or N, N- dimethylaminopyridine.

Als Lösungs- oder Verdünnungsmittel kommen alle inerten organischen Lösungsmittel in Betracht, beispielsweise aliphatische oder aromatische Kohlenwasserstoffe (wie Petrolether, Toluol), halogenierte Kohlenwasserstoffe (wie Chlortoluol, Dichlormethan, Chloroform, 1,2-Dichlorethan), Ether (wie Diethylether, Dioxan, Tetrahydrofuran, 1,2-Dimethoxyethan), Ester (wie Essigsäureethylester- oder - methylester), Nitrokohlenwasserstoffe (wie Nitromethan, Nitroethan, Nitrobenzol), Nitrile (wie Acetonitril, Benzonitril), Amide (wie N,N-Dimethylformamid, N,N-Dimethylacetamide, N-Methylformanilid, N-Methylpyrrolidon, Hexamethylphosphorsäuretriamid) sowie Dimethylsulfoxid oder Wasser oder Gemische der genannten Lösungsmittel.Suitable solvents or diluents are all inert organic solvents, for example aliphatic or aromatic hydrocarbons (such as petroleum ether, toluene), halogenated hydrocarbons (such as chlorotoluene, dichloromethane, chloroform, 1,2-dichloroethane), ethers (such as diethyl ether, dioxane, tetrahydrofuran , 1,2-dimethoxyethane), esters (such as ethyl acetate or methyl ester), nitrohydrocarbons (such as nitromethane, nitroethane, nitrobenzene), nitriles (such as acetonitrile, benzonitrile), amides (such as N, N- dimethylformamide, N, N- dimethylacetamides , N- methylformanilide, N- methylpyrrolidone, hexamethylphosphoric triamide) and dimethyl sulfoxide or water or mixtures of said solvents.

Zur Synthese der Verbindungen der Formel (A-III) können auch gemischte Anhydride (LG = COOR) eingesetzt werden (vgl. G. W. Anderson et al. J. Am. Chem. Soc. 1967, 89, 5012-5017 ). Bei diesem Verfahren, das über Verbindungen der Formel (A-II, LG = CO-OR, R = Alkyl, Aryl) führt, können Chlorameisensäureester zum Einsatz kommen, z.B. Chlorameisensäureisobutylester (LG = COOR mit R = iso-Butyl) und Chlorameisensäure-isopropylester (LG = COOR mit R = iso-Propyl). Ebenfalls können dafür Diethylacetylchlorid, Trimethylacetylchlorid und ähnliche Verbindungen verwendet werden.For the synthesis of the compounds of the formula (A-III) it is also possible to use mixed anhydrides (LG = COOR) (cf. GW Anderson et al. J. Am. Chem. Soc. 1967, 89, 5012-5017 ). In this process, which leads via compounds of the formula (A-II, LG = CO-OR, R = alkyl, aryl), chloroformates may be used, for example isobutyl chloroformate (LG = COOR with R = isobutyl) and chloroformic acid isopropyl ester (LG = COOR with R = iso-propyl). Also, diethylacetyl chloride, trimethylacetyl chloride and the like can be used therefor.

Methode A - Schritt 2: Die Amidfunktion der Carbonsäureamide des Typs (A-III) kann durch geeignete Schwefelungsreagenzien, z. B. Lawesson's Reagenz oder Phosphor(V)-sulfid, unter Erhitzen in einem geeigneten Lösungsmittel, z. B. Toluol oder Anisol, in eine Thioamidfunktion überführt werden, wodurch Verbindungen des Typs (A-IV) entstehen [vgl. z. B. EP 2 560 008 für N-(2,6-Dichlor-3-pyridyl)benzolcarbothioamid]. Bei diesem Reaktionstyp kann bereits teilweise, oder bei längerer Reaktionsdauer gegebenenfalls vollständig, eine Cyclisierung zu Verbindungen der Formel (I) erfolgen (vgl. z. B. WO 02/36580 für 2-Chlor-N-(2-chlor-pyridin-3-yl)-5-nitro-benzamid oder die weiter unten exemplarisch aufgeführte Synthese von 5-Chlor-2-(3-pyridyl)thiazolo[5,4-b]pyridin). Method A - Step 2: The amide function of the carboxylic acid amides of type (A-III) can be achieved by suitable sulfurization reagents, e.g. Lawesson's reagent or phosphorus (V) sulfide, with heating in a suitable solvent, e.g. As toluene or anisole, are converted into a thioamide function, whereby compounds of the type (A-IV) are formed [cp. z. B. EP 2 560 008 for N- (2,6-dichloro-3-pyridyl) benzenecarbothioamide]. In this type of reaction, it is possible in some cases, or for a longer reaction time, if appropriate completely, to cyclise to compounds of the formula (I) (cf. WO 02/36580 for 2-chloro-N- (2-chloro-pyridin-3-yl) -5-nitro-benzamide or the synthesis of 5-chloro-2- (3-pyridyl) thiazolo [5,4-b ] pyridine).

Methode A - Schritt 3: Schließlich lassen sich die Verbindungen der Formel (A-IV) nach literaturbekannten Methoden (vgl. z. B. EP 2 560 008 für 5-Chlor-2-phenyl-thiazolo[5,4-b]pyridin) durch Erhitzen in einem geeignetem Lösungsmittel, z. B. Toluol oder DMF, in Anwesenheit einer Base wie z. B. Natriumhydrid oder Kaliumcarbonat, in die Verbindungen der Formel (I) überführen. Method A - Step 3: Finally, the compounds of the formula (A-IV) can be prepared by methods known from the literature (cf. EP 2 560 008 for 5-chloro-2-phenyl-thiazolo [5,4-b] pyridine) by heating in a suitable solvent, e.g. For example, toluene or DMF, in the presence of a base such as. For example, sodium hydride or potassium carbonate, in the compounds of formula (I) convert.

Wird bei dem erfindungsgemäßen Verfahren zur Herstellung der Verbindungen der Formel (I) als Verbindung der Formel (A-I) 2,6-Dichlorpyridin-3-amin (R1 = H, R2 = Cl, X = Cl) und als Verbindung der Formel (A-II) 3-(Chlorcarbonyl)pyridiniumchlorid (A = 3-Pyridin-3-yl) eingesetzt, so entsteht zunächst das N-(2,6-Dichlorpyridin-2-yl)nicotinamid (entspricht A-IV mit A = 3-Pyridin-3-yl, R1 = H, R2 = Cl, X = Cl). Die nachfolgende Thionierung geht mit der Cyclisierung einher und führt direkt zum 5-Chlor-2-(3-pyridyl)thiazolo[5,4-b]pyridin, (entspricht (I) mit A = Pyridin-3-yl, R1 = H, R2 = Cl), vgl. auch die weiter unten exemplarisch aufgeführte Synthese von 5-Chlor-2-(3-pyridyl)thiazolo[5,4-b]pyridin.In the process according to the invention for the preparation of the compounds of the formula (I) as compound of the formula (AI), 2,6-dichloropyridin-3-amine (R 1 = H, R 2 = Cl, X = Cl) and as the compound of the formula first (A-II) of 3- (chlorocarbonyl) pyridinium chloride (A = 3-pyridin-3-yl) used, the result is the N - (2,6-Dichloro-pyridin-2-yl) nicotinamide (equivalent to A-IV A = 3-pyridin-3-yl, R 1 = H, R 2 = Cl, X = Cl). The subsequent thionation is accompanied by the cyclization and leads directly to 5-chloro-2- (3-pyridyl) thiazolo [5,4-b] pyridine, (corresponds to (I) with A = pyridin-3-yl, R 1 = H, R 2 = Cl), cf. also the synthesis of 5-chloro-2- (3-pyridyl) thiazolo [5,4-b] pyridine, which is listed below by way of example.

Die Verbindung 5-Chlor-2-(3-pyridyl)thiazolo[5,4-b]pyridin ist neu und auch Gegenstand der Erfindung.The compound 5-chloro-2- (3-pyridyl) thiazolo [5,4-b] pyridine is novel and also the subject of the invention.

Verbindungen der Formel (I), in denen R2 für Halogen, beispielsweise Chlor oder Brom, steht, können gemäß Reaktionsschema I aus halogenierten 2-Chlor-anilinderivaten (A-I) erhalten werden. Hieraus können nach literaturbekannten Methoden (B bis F) weitere Verbindungen der Formel (I) generiert werden. Beispielhaft sind die Methoden B bis F und die daraus resultierenden Verbindungstypen in Reaktionsschema II dargestellt.Compounds of the formula (I) in which R 2 is halogen, for example chlorine or bromine, can be obtained according to Reaction Scheme I from halogenated 2-chloroaniline derivatives (Al). From this, further compounds of the formula (I) can be generated by methods known from the literature (B to F). By way of example, methods B to F and the resulting compound types are shown in Reaction Scheme II.

Reaktionsschema II - Methoden B - FScheme II - Methods B - F

Figure imgb0270
Figure imgb0270

Methode B/F: Gemäß WO 2010/071819 bzw. WO 2010/008847 lassen sich chlorierte bzw. bromierte Thiazolopyridine mit gegebenenfalls in-situ erzeugten substituierten Arylboronsäuren bzw. Arylboronsäurepinakolestern in Anwesenheit von geeigneten Kupplungskatalysatoren, wie z. B. Tetrakis(triphenylphosphin)-palladium(0) oder [1,1'-Bis(diphenylphosphino)ferrocen]-dichlorpalladium(II) in Anwesenheit einer Base, wie z. B. Natriumcarbonat oder Natriumhydrogencarbonat, in einem inerten Lösungs- bzw. Verdünnungsmittel, wie z. B. 1,2-Dimethoxyethan oder 1,4-Dioxan in Kombination mit Wasser, arylieren (Methode B), wodurch Verbindungen der Formel (I-b) [vgl. auch Synthesebeispiel (1)] erhalten werden können. Auch gebenenfalls substituierte heteroaromatische Boronsäuren bzw. deren Pinakolester können analog mit chlorierten bicyclischen heteroaromatischen Systemen nach Methode B umgesetzt werden (vgl. z. B. WO 2010/071819 für 6-(6-Fluor-3-pyridyl)-2-[4-(1-piperidyl)-1-piperidyl]thiazolo[4,5-c]pyridin). Method B / F: According to WO 2010/071819 respectively. WO 2010/008847 can be chlorinated or brominated Thiazolopyridines with optionally in situ generated substituted arylboronic acids or Arylboronsäurepinakolestern in the presence of suitable coupling catalysts, such as. B. tetrakis (triphenylphosphine) palladium (0) or [1,1'-bis (diphenylphosphino) ferrocene] -dichlorpalladium (II) in the presence of a base such. For example, sodium carbonate or sodium bicarbonate, in an inert solvent or diluent, such as. As 1,2-dimethoxyethane or 1,4-dioxane in combination with water, arylation (Method B), whereby compounds of formula (Ib) [see. also Synthesis Example (1)] can be obtained. Also optionally substituted heteroaromatic boronic acids or their pinacol esters can be reacted analogously with chlorinated bicyclic heteroaromatic systems according to Method B (cf. WO 2010/071819 for 6- (6-fluoro-3-pyridyl) -2- [4- (1-piperidyl) -1-piperidyl] thiazolo [4,5-c] pyridine).

Außerdem lassen sich chlorierte Thiazolopyridine nach bekannten Methoden (vgl. Metal-Catalyzed Cross-Coupling Reactions (Eds.: A. de Meijere, F. Diederich), 2nd ed., Wiley-VCH, Weinheim, 2004 sowie Handbook of Organopalladium Chemistry for Organic Synthesis (Ed.: Ei-ichi Negishi), John Wiley & Sons, New York, 2002 ) mit gegebenenfalls substituierten aromatischen und heteroaromatischen Stannanen (LG = SnR3) in Gegenwart geeigneter Katalysatoren aus der Reihe der Übergangsmetallsalze zu Verbindungen der Formeln (I-b) umsetzen.In addition, chlorinated thiazolopyridines can be prepared by known methods (cf. Metal-Catalyzed Cross-Coupling Reactions (Ed .: A. de Meijere, F. Diederich), 2nd Ed., Wiley-VCH, Weinheim, 2004 such as Handbook of Organopalladium Chemistry for Organic Synthesis, John Wiley & Sons, New York, 2002 ) with optionally substituted aromatic and heteroaromatic stannanes (LG = SnR 3 ) in the presence of suitable catalysts from the series of transition metal salts to compounds of the formulas (Ib) implement.

Chlorierte Thiazolopyridine lassen sich mit 2-(Trialkylstannyl)pyrimidinen (in Analogie zu WO 2013/159064 ) in Anwesenheit von geeigneten Kupplungskatalysatoren, wie z.B. Tetrakis(triphenylphosphin)-palladium(0) in Kombination mit Kupfer(I)-iodid, in einem inerten Lösungs- bzw. Verdünnungsmittel, wie z.B. 1,4-Dioxan, arylieren. (vgl. auch Synthesebeispiel (7)).Chlorinated thiazolopyridines can be prepared with 2- (trialkylstannyl) pyrimidines (in analogy to WO 2013/159064 ) in the presence of suitable coupling catalysts, such as tetrakis (triphenylphosphine) palladium (0) in combination with copper (I) iodide, in an inert solvent or diluent, such as 1,4-dioxane. (See also Synthesis Example (7)).

Chlorierte Thiazolopyridine lassen sich auch nach bekannten Methoden (vgl. Metal-Catalyzed Cross-Coupling Reactions (Eds.: A. de Meijere, F. Diederich), 2nd ed., Wiley-VCH, Weinheim, 2004 sowie Handbook of Organopalladium Chemistry for Organic Synthesis (Ed.: Ei-ichi Negishi), John Wiley & Sons, New York, 2002 ) mit gegebenenfalls substituierten aromatischen und heteroaromatischen Arylzinkhalogeniden (LG = ZnX; X = Halogen) in Gegenwart geeigneter Katalysatoren aus der Reihe der Übergangsmetallsalze zu Verbindungen der Formeln (I-b) umsetzen. Chlorierte Thiazolopyridine (in Analogie zu Journal of Organic Chemistry (2010), 75, 8830 - 8832 ) lassen sich ferner mit 2-Pyridylzinkhalogeniden in Anwesenheit von geeigneten Katalysatorsystemen, wie z.B. Tris(dibenzylidenaceton)dipalladium in Kombination mit einem Liganden wie 2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, in einem inerten Lösungs- bzw. Verdünnungsmittel, wie z.B. Tetrahydrofuran, arylieren. (vgl. auch Synthesebeispiel (8)).Chlorinated thiazolopyridines can also be prepared by known methods (cf. Metal-Catalyzed Cross-Coupling Reactions (Ed .: A. de Meijere, F. Diederich), 2nd Ed., Wiley-VCH, Weinheim, 2004 such as Handbook of Organopalladium Chemistry for Organic Synthesis, John Wiley & Sons, New York, 2002 ) with optionally substituted aromatic and heteroaromatic arylzinc halides (LG = ZnX, X = halogen) in the presence of suitable catalysts from the series of transition metal salts to give compounds of the formulas (Ib). Chlorinated thiazolopyridines (in analogy to Journal of Organic Chemistry (2010), 75, 8830-8832 ) can also be reacted with 2-pyridylzinc halides in the presence of suitable catalyst systems such as tris (dibenzylideneacetone) dipalladium in combination with a ligand such as 2-dicyclohexylphosphino-2 ', 4', 6'-triisopropylbiphenyl in an inert solvent or diluent , such as tetrahydrofuran, arylate. (See also Synthesis Example (8)).

Die Strukturen (B-3) bis (B-9), (B-11) bis (B-13) und (B-21) bis (B-33) mit einer geeigneten Abgangsgruppe ("Leaving Group", LG = B(OH)2) oder (Hetero)arylboronsäureester (LG = B(OR)2) sind teilweise bekannt bzw. können nach bekannten Methoden hergestellt werden: z. B. 1-(Methyl-1H-pyrazol-4-yl)-boronsäure [(B-3), LG = B(OH)2, G2 = Wasserstoff, WO 2009/155527 ], 2-Phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-oxazol [(B-6), LG = B(OCMe2)2, G2 = Phenyl, WO 2010/094755 ]; Thiazol-2-yl-boronsäure [(B-7), LG = B(OH)2, G2 = Wasserstoff, US 6,310,095 B1 ]; 5-Phenyl-1,2,4-thiadiazol-3-yl-boronsäure [(B-13), LG = B(OH)2, G2 = Phenyl, DE 19710614 A1 ], Pyridin-3-yl-boronsäure [(B-21) vs (B-22), LG = B(OH)2, G2 = Wasserstoff, WO 2013/186089 ]; 1,3,5-Triazin-2-yl-boronsäure [(B-28), LG = B(OH)2, G2 = Wasserstoff, Korean Kongkae Taeho Kongbo ( 2011), KR 2011/079401 ].The structures (B-3) to (B-9), (B-11) to (B-13) and (B-21) to (B-33) having a suitable leaving group (" Leaving Group", LG = B (OH) 2 ) or (hetero) arylboronic acid esters (LG = B (OR) 2 ) are partially known or can be prepared by known methods: for. B. 1- (methyl-1 H- pyrazol-4-yl) boronic acid [(B-3), LG = B (OH) 2, G 2 = hydrogen, WO 2009/155527 ], 2-phenyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -oxazole [(B-6), LG = B (OCMe 2 ) 2 , G 2 = phenyl, WO 2010/094755 ]; Thiazol-2-ylboronic acid [(B-7), LG = B (OH) 2 , G 2 = hydrogen, US 6,310,095 B1 ]; 5-phenyl-1,2,4-thiadiazol-3-ylboronic acid [(B-13), LG = B (OH) 2 , G 2 = phenyl, DE 19710614 A1 ], Pyridin-3-ylboronic acid [(B-21) vs (B-22), LG = B (OH) 2 , G 2 = hydrogen, WO 2013/186089 ]; 1,3,5-triazin-2-ylboronic acid [(B-28), LG = B (OH) 2 , G 2 = hydrogen, Korean Kongkae Taeho Kongbo ( 2011), KR 2011/079401 ].

Verbindungen mit einer geeigneten Abgangsgruppe (LG = SnR3) sind teilweise bekannt bzw. können nach bekannten Methoden hergestellt werden: z.B. 5-Methyl-2-(tributylstannyl)-oxazol [(B-5), LG = SnBu3, G2 = Methyl, WO 2014/030128 A1 ]; 5-Ethyl-2-(tributylstannyl)-pyrimidin [(B-23), LG = SnBu3, G2 = Ethyl, WO 2003/039469 A2 ]; 2-Chloro-6-(tributylstannyl)-pyrazine [(B-26), LG = SnBu3, G2 = Cl, WO 2012/129338 A1 ].Compounds with a suitable leaving group (LG = SnR 3 ) are known in some cases or can be prepared by known methods: for example, 5-methyl-2- (tributylstannyl) -oxazole [(B-5), LG = SnBu 3 , G 2 = Methyl, WO 2014/030128 A1 ]; 5-ethyl-2- (tributylstannyl) -pyrimidine [(B-23), LG = SnBu 3 , G 2 = ethyl, WO 2003/039469 A2 ]; 2-chloro-6- (tributylstannyl) -pyrazines [(B-26), LG = SnBu 3 , G 2 = Cl, WO 2012/129338 A1 ].

Verbindungen mit einer geeigneten Abgangsgruppe (LG = ZnX, X = Halogen) sind teilweise bekannt bzw. können nach bekannten Methoden, ggf. auch in situ, hergestellt werden (vgl. dazu Handbook of Functionalized Organometallics (Ed.: P. Knochel), Wiley-VCH, Weinheim, 2005 ).Compounds with a suitable leaving group (LG = ZnX, X = halogen) are known in some cases or can be prepared by known methods, if appropriate also in situ (cf. Handbook of Functionalized Organometallics (Ed .: P. Knochel), Wiley-VCH, Weinheim, 2005 ).

Alternativ können die Verbindungen der Formel (I-a) zunächst mittels literaturbekannter Methoden in Verbindungen der Formel (I-h) überführt werden, die dann anschließend mit Halogen-aktivierten Heterocyclen gemäß Reaktionsschema II (Methode F) in einem inerten organischen Lösungs- bzw. Verdünnungsmittel analog zu Verbindungen der Formel (I-i) weiterreagieren (vgl. WO 2009/154775 bzw. WO 2010/116282 ).Alternatively, the compounds of the formula (Ia) can first be converted by methods known from the literature into compounds of the formula (Ih) which are then reacted with halogen-activated heterocycles according to Reaction Scheme II (Method F) in an inert organic solvent or diluent analogously to compounds continue to react the formula (Ii) (see. WO 2009/154775 respectively. WO 2010/116282 ).

Die Halogen-aktivierten Strukturen gemäß (B-3) bis (B-9), (B-11) bis (B-13) und (B-21) bis (B-33) sind teilweise bekannt bzw. können nach allgemein bekannten Methoden hergestellt werden: z. B. 3-Brom-4,5-dihydro-1-phenyl-1H-pyrazol [(B-18), LG = Br, G2 = Phenyl, J. Elguero et al., Bull. Soc. Chim. France 1996, 5, 1683-1686 ].The halogen-activated structures according to (B-3) to (B-9), (B-11) to (B-13) and (B-21) to (B-33) are partly known or can be known by well-known Methods are produced: z. B. 3-Bromo-4,5-dihydro-1-phenyl-1 H -pyrazole [(B-18), LG = Br, G 2 = phenyl, J. Elguero et al., Bull. Soc. Chim. France 1996, 5, 1683-1686 ].

Als Kupplungskatalysatoren kommen Palladium-Katalysatoren wie [1,1'-Bis(diphenylphosphino)ferrocen]dichlorpalladium (II) oder Tetrakis(triphenylphosphin) palladium in Betracht.Suitable coupling catalysts are palladium catalysts such as [1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium (II) or tetrakis (triphenylphosphine) palladium.

Als geeignete basische Reaktionshilfsmittel zur Durchführung der Verfahren gemäß Reaktionsschema III finden bevorzugt Carbonate des Natriums oder Kaliums Verwendung.Suitable basic reaction auxiliaries for carrying out the processes according to Reaction Scheme III are preferably carbonates of sodium or potassium.

Bevorzugt werden als Verdünnungsmittel Nitrile wie Acetonitril, Benzonitril, insbesondere Acetonitril, oder Ether wie Diethylether, Dioxan, Tetrahydrofuran, 1,2-Dimethoxyethan, insbesondere 1,2-Dimethoxyethan in Kombination mit Wasser eingesetzt.Preferred diluents are nitriles, such as acetonitrile, benzonitrile, in particular acetonitrile, or ethers, such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, in particular 1,2-dimethoxyethane, in combination with water.

Methode C: Chlorierte heteroaromatische Bicyclen lassen sich durch Erhitzen in Gegenwart von gegebenenfalls substituierten aliphatischen primären bzw. sekundären Aminen oder Arylmethyl- bzw. Method C: Chlorinated heteroaromatic bicycles can be prepared by heating in the presence of optionally substituted aliphatic primary or secondary amines or arylmethyl or

Hetarylmethylaminen in einem inerten organischen Lösungs- bzw. Verdünnungsmittel, wie z. B. Dimethylformamid, zu Verbindungen des (Typs (1-c), (1-d) und (1-e)) umsetzen. Diese Reaktion verläuft gegebenenfalls in Gegenwart einer geeigneten Base wie Kaliumcarbonat. (vgl. z. B. EP 2 560 008 zur Synthese von N-Benzyl-2-phenyl-thiazolo[5,4-b]pyridin-5-amin, und Synthesebeispiel (6)).Hetarylmethylaminen in an inert organic solvent or diluent, such as. As dimethylformamide, to compounds of the (type (1-c), (1-d) and (1-e)) implement. Optionally, this reaction proceeds in the presence of a suitable base such as potassium carbonate. (see eg. EP 2 560 008 for the synthesis of N- benzyl-2-phenyl-thiazolo [5,4-b] pyridin-5-amine, and Synthesis Example (6)).

Gegebenenfalls substituierte cyclische sekundäre Amine reagieren bevorzugt in Gegenwart geeigneter Kupplungskatalysatoren, wie z. B. Pd(OAc)2, und geeigneter Liganden, wie z. B. 2,2'-Bis-(diphenylphosphino)-1,1'-binaphthyl (BINAP), unter Zusatz einer Base wie beispielsweise Natrium-tert-butanolat und in Gegenwart eines inerten organischen Lösungs- bzw. Verdünnungsmittels, mit chlorierten heteroaromatischen Bicyclen zu Verbindungen der Formel (I-d). (vgl. z. B. WO 2007/148093 zur Synthese von 4-Pyridin-2-yl-morpholin und Synthesebeispiel (11)). Als Lösungs- oder Verdünnungsmittel kommen alle inerten organischen Lösungsmittel in Betracht, beispielsweise aliphatische oder aromatische Kohlenwasserstoffe. Bevorzugt werden aromatische Kohlenwasserstoffe wie beispielsweise Toluol eingesetzt.Optionally substituted cyclic secondary amines preferably react in the presence of suitable coupling catalysts, such as. B. Pd (OAc) 2 , and suitable ligands, such as. B. 2,2'-bis (diphenylphosphino) -1,1'-binaphthyl (BINAP), with the addition of a base such as sodium tert-butoxide and in the presence of an inert organic solvent or diluent, with chlorinated heteroaromatic Bicyclen to compounds of the formula (Id). (see eg. WO 2007/148093 for the synthesis of 4-pyridin-2-yl-morpholine and Synthesis Example (11)). Suitable solvents or diluents are all inert organic solvents, for example aliphatic or aromatic hydrocarbons. Preference is given to using aromatic hydrocarbons, for example toluene.

Methode D: Mit gegebenenfalls substituierten Anilinen reagieren chlorierte heteroaromatische Bicyclen in einem inerten organischen Lösungs- bzw. Verdünnungsmittel zu den entsprechenden Arylamino-Verbindungen der Formel (I-f) bevorzugt unter Katalyse durch geeignete Kupplungskatalysatoren wie z. B. Pd(OAc)2 oder Tris-(dibenzylidenaceton)-dipalladium(0), in Anwesenheit eines geeigneten Liganden, wie z. B. 2,2'-Bis-(diphenylphosphino)-1,1'-binaphthyl (BINAP) oder 2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, und einer Base, wie z. B. Natrium- oder Kalium-tert-butanolat (vgl. z. B. Bioorganic & Medicinal Chemistry 2012, 20, 5600 - 5615 zur Herstellung von tert-Butyl[5-({2-[(cyclopropylcarbonyl)amin][1,3]-thiazolo[5,4-b]pyridin-5-yl}amino)-2-flurophenyl]carbamat und Synthesebeispiel (9)). Method D: With optionally substituted anilines, chlorinated heteroaromatic bicyclics in an inert organic solvent or diluent react to form the corresponding arylamino compounds of the formula (If), preferably with catalysis by suitable coupling catalysts, such as, for example, B. Pd (OAc) 2 or tris (dibenzylideneacetone) dipalladium (0), in the presence of a suitable ligand, such as. B. 2,2'-bis (diphenylphosphino) -1,1'-binaphthyl (BINAP) or 2-dicyclohexylphosphino-2 ', 4', 6'-triisopropylbiphenyl, and a base such. For example, sodium or potassium tert-butoxide (see. Bioorganic & Medicinal Chemistry 2012, 20, 5600 - 5615 for preparing tert -butyl [5 - ({2 - [(cyclopropylcarbonyl) amine] [1,3] thiazolo [5,4- b ] pyridin-5-yl} amino) -2-flurophenyl] carbamate and Synthesis Example ( 9)).

Als Lösungs- oder Verdünnungsmittel kommen alle inerten organischen Lösungsmittel in Betracht, beispielsweise aliphatische oder aromatische Kohlenwasserstoffe. Bevorzugt werden aromatische Kohlenwasserstoffe wie beispielsweise Toluol eingesetzt oder Alkohole wie tert-Butanol.Suitable solvents or diluents are all inert organic solvents, for example aliphatic or aromatic hydrocarbons. Preference is given to using aromatic hydrocarbons, for example toluene, or alcohols, such as tert-butanol.

Verbindungen der Formel (I), in denen R2 für -NHR22 (vgl. Formel (1-f)) steht, lassen sich in Verbindungen der Formel (I), in denen R2 für -NR23R22 steht, durch Alkylierung mit geeigneten Elektrophilen überführen. Diese Reaktion erfolgt gegebenenfalls in Gegenwart einer Base, wie z.B. Natriumhydrid, und in einem organischen Lösungs- bzw. Verdünnungsmittel. Bevorzugt kommen dabei Amide, wie z.B. Dimethylformamid, zum Einsatz. Als Elektrophile dienen bevorzugt Alkylhalogenide der Formel R23-X, wobei R23 in diesem Fall insbesondere für Alkyl, Cycloalkyl, Alkylthioalkyl, Cyanoalkyl und Alkoxyalkyl und X für Halogen, wie Iod, Brom oder Chlor, steht (siehe Synthesebeispiel (14)).Compounds of the formula (I) in which R 2 is -NHR 22 (compare formula (1-f)) can be converted into compounds of the formula (I) in which R 2 is -NR 23 R 22 Transfer alkylation with suitable electrophiles. This reaction is optionally carried out in the presence of a base, such as sodium hydride, and in an organic solvent or diluent. Amides such as dimethylformamide are preferably used. Preferred electrophiles are alkyl halides of the formula R 23 -X, in which case R 23 is in particular alkyl, cycloalkyl, alkylthioalkyl, cyanoalkyl and alkoxyalkyl and X is halogen, such as iodine, bromine or chlorine (see Synthesis Example (14)).

Methode E: Gegebenenfalls substituierte Heterocyclen wie beispielsweise Imidazole, Pyrazole und Triazole, lassen sich in Anlehnung an die im Reaktionsschema II gezeigte literaturbekannte Methode E, bevorzugt in Gegenwart geeigneter Katalysatoren wie z.B. Kupfer(I)iodid, in Anwesenheit basischer Liganden, z. B. trans-N,N'-Dimethylcyclohexan-1,2-diamin, und einer Base wie Kaliumcarbonat, in einem inerten organischen Lösungs- bzw. Verdünnungsmittel in chlorierte bicyclische Systeme einführen (siehe Journal of Organic Chemistry (2010), 69, 5578 , vergleiche auch Synthesebeispiel (13)). Method E: Optionally substituted heterocycles, such as, for example, imidazoles, pyrazoles and triazoles, can be prepared on the basis of the literature-known method E shown in Reaction Scheme II, preferably in the presence of suitable catalysts such as copper (I) iodide, in the presence of basic ligands, eg. Trans -N, N'-dimethylcyclohexane-1,2-diamine, and a base such as potassium carbonate, in an inert organic solvent or diluent, respectively, into chlorinated bicyclic systems (see Journal of Organic Chemistry (2010), 69, 5578 , see also Synthesis Example (13)).

Als Lösungs- oder Verdünnungsmittel kommen alle inerten organischen Lösungsmittel in Betracht, beispielsweise aliphatische oder aromatische Kohlenwasserstoffe. Bevorzugt werden aromatische Kohlenwasserstoffe wie beispielsweise Toluol eingesetzt, aber auch polarere Lösungsmittel wie DMF.Suitable solvents or diluents are all inert organic solvents, for example aliphatic or aromatic hydrocarbons. Preference is given to using aromatic hydrocarbons such as, for example, toluene, but also more polar solvents such as DMF.

Verbindungen der Formel (I-a) können gemäß Reaktionsschema I erhalten werden. Hieraus können nach literaturbekannten Methoden (G) Verbindungen der Formel (I) generiert werden, wie in Reaktionsschema III dargestellt.Compounds of the formula (I-a) can be obtained according to Reaction Scheme I. From this, compounds of the formula (I) can be generated by methods known from the literature (G), as shown in Reaction Scheme III.

Reaktionsschema III - Methode GReaction Scheme III - Method G

Figure imgb0271
Figure imgb0271

Methode G - Schritt 1: Verbindungen der Formel (I-a) können nach literaturbekannten Methoden mit Kohlenmonoxid und einem Alkohol, z. B. Methanol, unter Katalyse durch geeignete Metallverbindungen in Kombination mit geeigneten Liganden wie z. B. Palladium(II)-acetat in Kombination mit 1,3-Bis(diphenylphosphino)propan, und in Anwesenheit von Basen wie Triethylamin oder Kaliumcarbonat, in geeigneten Lösungsmitteln wie z. B. dem verwendeten Alkohol selbst, THF und/oder DMF, zu den entsprechenden Carbonsäureestern der Formel (I-j) umgesetzt werden [vgl. WO 2007/016392 für Methyl-2-(isopropylamino)thiazolo[5,4-b]pyridin-5-carboxylat]. Method G - Step 1: Compounds of formula (Ia) can be prepared by literature methods with carbon monoxide and an alcohol, for. As methanol, with catalysis by suitable metal compounds in combination with suitable ligands such. B. palladium (II) acetate in combination with 1,3-bis (diphenylphosphino) propane, and in the presence of bases such as triethylamine or potassium carbonate, in suitable solvents such. B. the alcohol itself, THF and / or DMF, to the corresponding carboxylic acid esters of the formula (Ij) are reacted [see. WO 2007/016392 for methyl 2- (isopropylamino) thiazolo [5,4-b] pyridine-5-carboxylate].

Methode G - Schritt 2: Ester der Formel (I-j) können nach literaturbekannten Methoden mittels geeigneter Basen, wie z. B. wässriger Lithiumhydroxid- oder Natriumhydroxid-Lösung, in geeigneten Lösungs- bzw. Verdünnungsmitteln, wie z. B. Dioxan oder THF, in Verbindungen der Formel (I-k) mit freier Säurefunktion überführt werden. Method G - Step 2: Esters of the formula (Ij) can be prepared by methods known from the literature by means of suitable bases, such as. As aqueous lithium hydroxide or sodium hydroxide solution, in suitable solvents or diluents, such as. As dioxane or THF, in compounds of formula (Ik) are transferred with free acid function.

Methode G - Schritt 3: Verbindungen der Formel (I), in denen R2 für einen Rest aus der Reihe (C-1) bis (C-9) oder für -C(X)-NR22R23 steht, können aus Verbindungen der Formel (I-k) nach geeigneter Aktivierung (d.h. LG steht für eine gegebenenfalls in-situ erzeugte nucleofuge Abgangsgruppe) mittels bekannter Methoden hergestellt werden [vgl. Methode A, Schritt 1]. Method G - Step 3: Compounds of the formula (I) in which R 2 is a radical from the series (C-1) to (C-9) or -C (X) -NR 22 R 23 can be prepared from Compounds of the formula (Ik) after appropriate activation (ie LG represents an optionally in situ generated nucleofuge leaving group) can be prepared by known methods [cf. Method A, step 1].

Beispielsweise können die Verbindungen der Formel (I), in denen R2 für einen Rest (C-1) oder für-C(X)NR22R23 steht, gemäß Reaktionsschema III erhalten werden.For example, the compounds of formula (I) wherein R 2 is (C-1) or C (X) NR 22 R 23 can be obtained according to Reaction Scheme III.

Als Kondensationsmittel zur Aktivierung der Carbonsäuren der Formel (I-k) kommen alle üblicherweise für derartige Amidierungsreaktionen verwendbaren Kondensationsmittel infrage.Suitable condensing agents for activating the carboxylic acids of the formula (I-k) are all condensing agents customarily used for such amidation reactions.

Methode G - Schritt 4: Die nachfolgenden Reaktionen der aktivierten Verbindungen der Formel (I-l) mit den jeweiligen Komponenten nach Reaktionsschema III wird gegebenenfalls in Gegenwart eines geeigneten Reaktionshilfstoffes und in Gegenwart eines geeigneten Lösungs- oder Verdünnungsmittels durchgeführt. Method G - Step 4: The subsequent reactions of the activated compounds of the formula (II) with the respective components according to Reaction Scheme III are optionally carried out in the presence of a suitable reaction auxiliary and in the presence of a suitable solvent or diluent.

Als geeignete Reaktionshilfsstoffe finden basische Reaktionshilfsmittel zur Durchführung der Verfahren gemäss Reaktionsschema IV Verwendung.Suitable reaction auxiliaries are basic reaction auxiliaries for carrying out the processes according to Reaction Scheme IV.

Als basische Reaktionshilfsmittel können alle geeigneten Säurebindemittel eingesetzt werden, beispielsweise Amine, insbesondere tertiäre Amine, sowie Alkali- und Erdalkaliverbindungen.As basic reaction auxiliaries it is possible to use all suitable acid binders, for example amines, in particular tertiary amines, and also alkali metal and alkaline earth metal compounds.

Zur Herstellung von Verbindungen der Formeln (I-m) und (I-n) werden vorzugsweise tertiäre Amine wie N-Propyl-diisopropylamin oder N-Ethyl-diisopropylamin (DIEA; Hünig's Base) eingesetzt.For the preparation of compounds of the formulas (Im) and (In) tertiary amines such as N- propyl-diisopropylamine or N- ethyl-diisopropylamine (DIEA, Hünig's base) are preferably used.

Als geeignete Lösungs- oder Verdünnungsmittel kommen alle inerten organischen Lösungsmittel in Betracht.Suitable solvents or diluents are all inert organic solvents.

Bevorzugt werden Amide, beispielsweise N,N-Dimethylformamid, als Lösungsmittel eingesetzt.Preference is given to using amides, for example N, N- dimethylformamide, as solvent.

Verbindungen der Formel (I), in denen R2 für -NR23-C(X)-R22 steht, können beispielsweise aus Verbindungen der Formel (I), in denen R2 für -NHR23 steht, mittels N-Acylierungsreaktion unterCompounds of the formula (I) in which R 2 is -NR 23 -C (X) -R 22 can, for example, be obtained from compounds of the formula (I) in which R 2 is -NHR 23 by means of an N-acylation reaction

Verwendung von aktivierten Verbindungen der Formel LG-C(X)-R22, worin LG für eine gegebenenfalls in-situ erzeugte nucleofuge Abgangsgruppe steht, erhalten werden.Use of activated compounds of the formula LG-C (X) -R 22 , wherein LG is an optionally in situ generated nucleofuge leaving group, can be obtained.

Diese Verbindungen der Formel (I), in denen R2 für -NHR23 steht, lassen sich aus Verbindungen der Formel (I-k) gemäß Reaktionsschema IV darstellen.These compounds of the formula (I) in which R 2 is -NHR 23 can be prepared from compounds of the formula (Ik) according to Reaction Scheme IV.

Reaktionsschema IV - Methode HReaction Scheme IV - Method H

Figure imgb0272
Figure imgb0272

Beispielsweise können Verbindungen der Formel (I-o) mittels Curtius-Abbau, wie beispielsweise in Houben-Weyl, Methoden der Organischen Chemie, Band XI/1 (Georg Thieme Verlag Stuttgart), S. 865 beschrieben, erhalten werden.For example, compounds of formula (Io) may be degraded by Curtius degradation, such as in Houben-Weyl, Methods of Organic Chemistry, Volume XI / 1 (Georg Thieme Verlag Stuttgart), p. 865 described, can be obtained.

Hierbei können die Verbindungen der Formel (I-k) beispielsweise mit Diphenylphosphorylazid (DPPA) in Gegenwart von tert-Butanol direkt zu Verbindungen der Formel (I-o) reagieren.In this case, the compounds of the formula (Ik) can react, for example, with diphenylphosphoryl azide (DPPA) in the presence of tert- butanol directly to give compounds of the formula (Io).

Des Weiteren können Verbindungen der Formel (I, wobei R2 = Halogen) durch Austausch des Halogens, z.B. Brom oder Chlor, mit tert-Butylcarbamat, unter Katalyse durch geeignete Metallverbindungen z. B. Palladium(II)-acetat ggf. in Kombination mit geeigneten Liganden wie z.B. 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthen, und in Anwesenheit von Basen wie Caesiumcarbonat, in geeigneten Lösungsmitteln wie z. B. 1,4-Dioxan, zu den entsprechenden Carbamaten des Typs (I-o) umgesetzt werden (vgl. Journal of Medicinal Chemistry (2011), 54, 1511 - 1528 ).Furthermore, compounds of formula (I, wherein R 2 = halogen) by exchange of the halogen, for example bromine or chlorine, with tert-butyl carbamate, with catalysis by suitable metal compounds z. B. palladium (II) acetate optionally in combination with suitable ligands such as 4,5-bis (diphenylphosphino) -9,9-dimethylxanthene, and in the presence of bases such as cesium carbonate, in suitable solvents such. As 1,4-dioxane, to the corresponding carbamates of the type (Io) are reacted (see. Journal of Medicinal Chemistry (2011), 54, 1511-1528 ).

Aus den Verbindungen der Formel (I-o) lassen sich die Verbindungen der Formeln (I-p) durch N-Alkylierung in einem ersten Reaktionsschritt, N-Deblockierung (d.h. Abspaltung der Boc-Gruppe) in einem zweiten Reaktionsschritt und nachfolgende N-Acylierung in einem dritten Reaktionsschritt erhalten.From the compounds of the formula (Io), the compounds of the formulas (Ip) can be obtained by N-alkylation in a first reaction step, N -diblocking (ie cleavage of the Boc group) in a second reaction step and subsequent N- acylation in a third reaction step receive.

Die Verbindungen der Formel (I-q) können mittels N-Deblockierung (d.h. Abspaltung der Boc-Gruppe) in einem ersten Reaktionsschritt und nachfolgender N-Acylierung in einem zweiten Reaktionsschritt hergestellt werden.The compounds of the formula (Iq) can be prepared by N- blocking (ie cleavage of the Boc group) in a first reaction step and subsequent N- acylation in a second reaction step.

Die Verbindungen der Formel (I-p) können ebenfalls durch durch N-Alkylierung aus den Verbindungen der Formel (I-q) erhalten werden.The compounds of the formula (Ip) can also be obtained by N- alkylation from the compounds of the formula (Iq).

Des Weiteren können Verbindungen der Formel (I-p) durch N-Acylierung von Verbindungen der Formel (I-c) erhalten werden.Furthermore, compounds of the formula (Ip) can be obtained by N- acylation of compounds of the formula (Ic).

Im Allgemeinen können für die Entfernung der Schutzgruppe saure oder basische Reaktionshilfsmittel nach literaturbekannter Verfahrensweise verwendet werden. Bei Verwendung von Schutzgruppen des Carbamat-Typs werden bevorzugt saure Reaktionshilfsmittel verwendet. Bei Verwendung der tert-Butylcarbamat-Schutzgruppe (Boc-Gruppe) werden beispielsweise Mischungen von Mineralsäuren wie Salzsäure, Bromwasserstoffsäure, Salpetersäure, Schwefelsäure, Phosphorsäure oder von organischen Säuren wie Benzoesäure, Ameisensäure, Essigsäure, Trifluoressigsäure, Methansulfonsäure, Benzolsulfonsäure oder Toluolsulfonsäure in einem geeigneten Verdünnungsmittel wie Wasser und/oder einem organischen Lösungsmittel wie Tetrahydrofuran, Dioxan, Dichlormethan, Chloroform, Essigester, Ethanol oder Methanol verwendet. Bevorzugt sind Mischungen von Salzsäure oder Essigsäure mit Wasser und/oder einem organischen Lösungsmittel wie Essigester.In general, acidic or basic reaction auxiliaries can be used according to the literature procedure for the removal of the protective group. When using carbamate-type protecting groups, preference is given to using acidic reaction auxiliaries. When using the tert- butylcarbamate protective group (Boc group), for example, mixtures of mineral acids such as hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, phosphoric acid or organic acids such as benzoic acid, formic acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, benzenesulfonic acid or toluenesulfonic acid in a suitable diluent such as water and / or an organic solvent such as tetrahydrofuran, dioxane, dichloromethane, chloroform, ethyl acetate, ethanol or methanol. Preference is given to mixtures of hydrochloric acid or acetic acid with water and / or an organic solvent such as ethyl acetate.

Methode I - Allgemeine Verfahren für die Oxidation von Thioethern zu Sulfoxiden und SulfonenMethod I - General procedures for the oxidation of thioethers to sulfoxides and sulfones

Verbindungen der Formel (I), in welchen W für SO (Sulfoxide) oder für SO2 (Sulfone) steht, lassen sich nach literaturbekannten Verfahren durch Oxidation aus Verbindungen der Formel (I), in welchen W für S (Thioethern) herstellen, beispielsweise durch ein Oxidationsmittel in einem geeigneten Lösungs- bzw. Verdünnungsmittel. Als Oxidationsmittel eignen sich zum Beispiel verdünnte Salpetersäure, Wasserstoffperoxid, Oxone® und Peroxycarbonsäuren, wie etwa meta-Chlorperbenzoesäure. Als Lösungsmittel bzw. Verdünnungsmittel eignen sich inerte organische Lösungsmittel, typischerweise Acetonitril und halogenierte Lösungsmittel wie Dichlormethan, Chloroform oder Dichlorethan, sowie Wasser und Alkohole wie Methanol für die Reaktion mit Oxone®.Compounds of the formula (I) in which W is SO (sulfoxides) or SO 2 (sulfones) can be prepared by methods known from the literature by oxidation from compounds of the formula (I) in which W is S (thioethers), for example by an oxidizing agent in a suitable solution or Diluent. Suitable oxidizing agents are, for example, dilute nitric acid, hydrogen peroxide, Oxone® and peroxycarboxylic acids, such as meta- chloroperbenzoic acid. Suitable solvents or diluents are inert organic solvents, typically acetonitrile and halogenated solvents such as dichloromethane, chloroform or dichloroethane, and water and alcohols such as methanol for the reaction with Oxone®.

Möglich ist auch die Einführung geeigneter Aniline R1-NH2 oder Boronsäuren R1-B(OH)2, in welchen W für SO oder SO2 steht, nach Verfahren B bzw. D. Diese lassen sich auf den entsprechenden Vorstufen, in denen W für S steht, nach literaturbekannten Verfahren oxidieren, wie zum Beispiel in WO 2013/092350 beschrieben.It is also possible to introduce suitable anilines R 1 -NH 2 or boronic acids R 1 -B (OH) 2 , in which W is SO or SO 2 , by methods B and D. These can be determined on the corresponding precursors in which W stands for S, oxidize according to literature methods, such as in WO 2013/092350 described.

Zur Erzeugung enantiomeren angereicherter Sulfoxide eignen sich eine Vielfalt von Methoden, wie von G. E. O'Mahony et al., in ARKIVOC (Gainesville, FL, United states), 2011, 1, 1-110 , beschrieben: Metall-katalysierte asymmetrische Oxidationen von Thioethern, zum Beispiel mit Titanium oder Vanadium als meistbenutzten Katalysatorquellen, in Form von Ti(OiPr4) oder VO(acac)2, zusammen mit einem chiralen Liganden und einem Oxidationsmittel wie tert-Butylwasserstoffperoxid (TBHP), 2-Phenylpropan-2-ylhydroperoxid (CHP) oder Wasserstoffperoxid; nicht-metall katalysierte asymmetrische Oxidationen durch Verwendung von chiralen Oxidationsmitteln oder chiralen Katalysatoren; elektrochemische oder biologische asymmetrische Oxidationen sowie kinetische Resolution von Sulfoxiden und nukleophilische Versetzung (nach Andersens Methode).To produce enantiomerically enriched sulfoxides, a variety of methods, such as GE O'Mahony et al., In ARKIVOC (Gainesville, FL, United states), 2011, 1, 1-110 described: metal-catalyzed asymmetric oxidations of thioethers, for example with titanium or vanadium as the most commonly used catalyst sources, in the form of Ti (O i Pr 4 ) or VO (acac) 2 , together with a chiral ligand and an oxidizing agent such as tert-butyl hydrogen peroxide (TBHP), 2-phenylpropan-2-yl hydroperoxide (CHP) or hydrogen peroxide; non-metal catalyzed asymmetric oxidations by using chiral oxidants or chiral catalysts; electrochemical or biological asymmetric oxidation as well as kinetic resolution of sulfoxides and nucleophilic displacement (according to Andersen's method).

Die Enantiomere können auch aus dem Racemat gewonnen werden, beispielsweise durch präparative Trennung mittels einer chiralen HPLC.The enantiomers can also be obtained from the racemate, for example by preparative separation by means of a chiral HPLC.

Wenn im Folgenden von Verbindungen der Formel (I) die Rede ist, sind auch diejenigen Verbindungen in der Tabelle 1 eingeschlossen, die nicht unter die Formel (I) fallen.When referring in the following to compounds of the formula (I), those compounds are also included in Table 1 which do not fall under the formula (I).

Isomereisomers

Die Verbindungen der Formel (I) können in Abhängigkeit von der Art der Substituenten als geometrische und/oder als optisch aktive Isomere oder entsprechende Isomerengemische in unterschiedlicher Zusammensetzung vorliegen. Diese Stereoisomere sind beispielsweise Enantiomere, Diastereomere, Atropisomere oder geometrische Isomere. Die Erfindung umfasst somit reine Stereo¬isomere als auch beliebige Gemische dieser Isomere.Depending on the nature of the substituents, the compounds of the formula (I) can be present as geometrical and / or as optically active isomers or corresponding isomer mixtures in different compositions. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers. The invention thus comprises pure stereoisomers as well as any mixtures of these isomers.

Verfahren und VerwendungenMethods and uses

Die Erfindung betrifft auch Verfahren zur Bekämpfung von tierischen Schädlingen, bei dem man Verbindungen der Formel (I) auf tierische Schädlinge und/oder ihren Lebensraum einwirken lässt. Bevorzugt wird die Bekämpfung der tierischen Schädlinge in der Land- und Forstwirtschaft und im Materialschutz durchgeführt. Hierunter vorzugsweise ausgeschlossen sind Verfahren zur chirurgischen oder therapeutischen Behandlung des menschlichen oder tierischen Körpers und Diagnostizierverfahren, die am menschlichen oder tierischen Körper vorgenommen werden.The invention also relates to methods for controlling animal pests, in which compounds of the formula (I) are allowed to act on animal pests and / or their habitat. Preference is given to the control of animal pests in agriculture and forestry and in the protection of materials. Among these, preferably excluded are methods for surgical or therapeutic treatment of the human or animal body and diagnostic procedures that are performed on the human or animal body.

Die Erfindung betrifft ferner die Verwendung der Verbindungen der Formel (I) als Schädlingsbekämpfungsmittel, insbesondere Pflanzenschutzmittel.The invention further relates to the use of the compounds of the formula (I) as pesticides, in particular pesticides.

Im Rahmen der vorliegenden Anmeldung umfasst der Begriff Schädlingsbekämpfungsmittel immer auch den Begriff Pflanzenschutzmittel.In the context of the present application, the term pest control always includes the term pesticides.

Die Verbindungen der Formel (I) eignen sich bei guter Pflanzenverträglichkeit, günstiger Warmblütertoxizität und guter Umweltverträglichkeit zum Schutz von Pflanzen und Pflanzenorganen vor biotischen und abiotischen Stressfaktoren, zur Steigerung der Ernteerträge, Verbesserung der Qualität des Erntegutes und zur Bekämpfung von tierischen Schädlingen, insbesondere Insekten, Spinnentieren, Helminthen, Nematoden und Mollusken, die in der Landwirtschaft, im Gartenbau, bei der Tierzucht, in Aquakulturen, in Forsten, in Gärten und Freizeiteinrichtungen, im Vorrats- und Materialschutz sowie auf dem Hygienesektor vorkommen. Sie können vorzugsweise als Schädlingsbekämpfungsmittel eingesetzt werden. Sie sind gegen normal sensible und resistente Arten sowie gegen alle oder einzelne Entwicklungsstadien wirksam. Zu den oben erwähnten Schädlingen gehören:
Schädlinge aus dem Stamm der Arthropoda, insbesondere aus der Klasse der Arachnida z.B. Acarus spp., z.B. Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., z.B. Aculus fockeui, Aculus schlechtendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., z.B. Brevipalpus phoenicis, Bryobia graminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp., z.B. Eotetranychus hicoriae, Epitrimerus pyri, Eutetranychus spp., z.B. Eutetranychus banksi, Eriophyes spp., z.B. Eriophyes pyri, Glycyphagus domesticus, Halotydeus destructor, Hemitarsonemus spp., z.B. Hemitarsonemus latus (=Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp., Latrodectus spp., Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp., Oligonychus spp., z.B. Oligonychus coniferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychus pratensis, Oligonychus punicae, Oligonychus yothersi, Ornithodorus spp., Ornithonyssus spp., Panonychus spp., z.B. Panonychus citri (=Metatetranychus citri), Panonychus ulmi (=Metatetranychus ulmi), Phyllocoptruta oleivora, Platytetranychus multidigituli, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemus spp., Steneotarsonemus spinki, Tarsonemus spp., z.B. Tarsonemus confusus, Tarsonemus pallidus, Tetranychus spp., z.B. Tetranychus canadensis, Tetranychus cinnabarinus, Tetranychus turkestani, Tetranychus urticae, Trombicula alfreddugesi, Vaejovis spp., Vasates lycopersici;
aus der Klasse der Chilopoda z.B. Geophilus spp., Scutigera spp.;
aus der Ordnung oder der Klasse der Collembola z.B. Onychiurus armatus; Sminthurus viridis;
aus der Klasse der Diplopoda z.B. Blaniulus guttulatus;
aus der Klasse der Insecta, z.B. aus der Ordnung der Blattodea z.B. Blatta orientalis, Blattella asahinai, Blattella germanica, Leucophaea maderae, Panchlora spp., Parcoblatta spp., Periplaneta spp., z.B. Periplaneta americana, Periplaneta australasiae, Supella longipalpa;
aus der Ordnung der Coleoptera z.B. Acalymma vittatum, Acanthoscelides obtectus, Adoretus spp., Agelastica alni, Agriotes spp., z.B. Agriotes linneatus, Agriotes mancus, Alphitobius diaperinus, Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., Anthonomus spp., z.B. Anthonomus grandis, Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp., z.B. Atomaria linearis, Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp., z.B. Bruchus pisorum, Bruchus rufimanus, Cassida spp., Cerotoma trifurcata, Ceutorrhynchus spp., z.B. Ceutorrhynchus assimilis, Ceutorrhynchus quadridens, Ceutorrhynchus rapae, Chaetocnema spp., z.B. Chaetocnema confinis, Chaetocnema denticulata, Chaetocnema ectypa, Cleonus mendicus, Conoderus spp., Cosmopolites spp., z.B. Cosmopolites sordidus, Costelytra zealandica, Ctenicera spp., Curculio spp., z.B. Curculio caryae, Curculio caryatrypes,Curculio obtusus, Curculio sayi, Cryptolestes ferrugineus, Cryptolestes pusillus, Cryptorhynchus lapathi, Cryptorhynchus mangiferae, Cylindrocopturus spp., Cylindrocopturus adspersus, Cylindrocopturus furnissi, Dermestes spp., Diabrotica spp., z.B. Diabrotica balteata, Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp., Dicladispa armigera, Diloboderus spp., Epilachna spp., z.B. Epilachna borealis, Epilachna varivestis, Epitrix spp., z.B. Epitrix cucumeris, Epitrix fuscula, Epitrix hirtipennis, Epitrix subcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides, Gnathocerus cornutus, Hellula undalis, Heteronychus arator, Heteronyx spp., Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypomeces squamosus, Hypothenemus spp., z.B. Hypothenemus hampei, Hypothenemus obscurus, Hypothenemus pubescens, Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsa decemlineata, Leucoptera spp., z.B. Leucoptera coffeella, Lissorhoptrus oryzophilus, Lixus spp., Luperomorpha xanthodera, Luperodes spp., Lyctus spp., Megascelis spp., Melanotus spp., z.B. Melanotus longulus oregonensis, Meligethes aeneus, Melolontha spp., z.B. Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorhynchus spp., z.B. Otiorhynchus cribricollis, Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Phyllophaga helleri, Phyllotreta spp., z.B. Phyllotreta armoraciae, Phyllotreta pusilla, Phyllotreta ramosa, Phyllotreta striolata, Popillia japonica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp., z.B. Psylliodes affinis, Psylliodes chrysocephala, Psylliodes punctulata, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp., z.B. Sitophilus granarius, Sitophilus linearis, Sitophilus oryzae, Sitophilus zeamais, Sphenophorus spp., Stegobium paniceum, Sternechus spp., z.B. Sternechus paludatus, Symphyletes spp., Tanymecus spp., z.B. Tanymecus dilaticollis, Tanymecus indicus, Tanymecus palliatus, Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp., z.B. Tribolium audax, Tribolium castaneum, Tribolium confusum, Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., z.B. Zabrus tenebrioides;
aus der Ordnung der Diptera z.B. Aedes spp., z.B. Aedes aegypti, Aedes albopictus, Aedes sticticus, Aedes vexans, Agromyza spp., z.B. Agromyza frontella, Agromyza parvicornis, Anastrepha spp., Anopheles spp., z.B. Anopheles quadrimaculatus, Anopheles gambiae, Asphondylia spp., Bactrocera spp., z.B. Bactrocera cucurbitae, Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata, Chironomus spp., Chrysomya spp., Chrysops spp., Chrysozona pluvialis, Cochliomya spp., Contarinia spp., z.B. Contarinia johnsoni, Contarinia nasturtii, Contarinia pyrivora, Contarinia schulzi, Contarinia sorghicola, Contarinia tritici,Cordylobia anthropophaga, Cricotopus sylvestris, Culex spp., z.B. Culex pipiens, Culex quinquefasciatus, Culicoides spp., Culiseta spp., Cuterebra spp., Dacus oleae, Dasineura spp., z.B. Dasineura brassicae, Delia spp., z.B. Delia antiqua, Delia coarctata, Delia florilega, Delia platura, Delia radicum, Dermatobia hominis, Drosophila spp., z.B. Drosphila melanogaster, Drosophila suzukii, Echinocnemus spp., Fannia spp., Gasterophilus spp., Glossina spp., Haematopota spp., Hydrellia spp., Hydrellia griseola, Hylemya spp., Hippobosca spp., Hypoderma spp., Liriomyza spp., z.B. Liriomyza brassicae, Liriomyza huidobrensis, Liriomyza sativae, Lucilia spp., z.B. Lucilia cuprina, Lutzomyia spp., Mansonia spp., Musca spp., z.B. Musca domestica, Musca domestica vicina, Oestrus spp., Oscinella frit, Paratanytarsus spp., Paralauterborniella subcincta, Pegomya spp., z.B. Pegomya betae, Pegomya hyoscyami, Pegomya rubivora, Phlebotomus spp., Phorbia spp., Phormia spp., Piophila casei, Prodiplosis spp., Psila rosae, Rhagoletis spp., z.B. Rhagoletis cingulata, Rhagoletis completa, Rhagoletis fausta, Rhagoletis indifferens, Rhagoletis mendax, Rhagoletis pomonella, Sarcophaga spp., Simulium spp., z.B. Simulium meridionale, Stomoxys spp., Tabanus spp., Tetanops spp., Tipula spp., z.B. Tipula paludosa, Tipula simplex;
aus der Ordnung der Hemiptera z.B. Acizzia acaciaebaileyanae, Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosipon spp., z.B. Acyrthosiphon pisum, Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleyrodes proletella, Aleurolobus barodensis, Aleurothrixus floccosus, Allocaridara malayensis, Amrasca spp., z.B. Amrasca bigutulla, Amrasca devastans, Anuraphis cardui, Aonidiella spp., z.B. Aonidiella aurantii, Aonidiella citrina, Aonidiella inornata, Aphanostigma piri, Aphis spp., z.B. Aphis citricola, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis glycines, Aphis gossypii, Aphis hederae, Aphis illinoisensis, Aphis middletoni, Aphis nasturtii, Aphis nerii, Aphis pomi, Aphis spiraecola, Aphis viburniphila, Arboridia apicalis, Arytainilla spp., Aspidiella spp., Aspidiotus spp., z.B. Aspidiotus nerii, Atanus spp., Aulacorthum solani, Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae, Brachycaudus helichrysi, Brachycolus spp., Brevicoryne brassicae, Cacopsylla spp., z.B. Cacopsylla pyricola, Calligypona marginata, Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chondracris rosea, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp., z.B. Coccus hesperidum, Coccus longulus, Coccus pseudomagnoliarum, Coccus viridis, Cryptomyzus ribis, Cryptoneossa spp., Ctenarytaina spp., Dalbulus spp., Dialeurodes citri, Diaphorina citri, Diaspis spp., Drosicha spp., Dysaphis spp., z.B. Dysaphis apiifolia, Dysaphis plantaginea, Dysaphis tulipae, Dysmicoccus spp., Empoasca spp., z.B. Empoasca abrupta, Empoasca fabae, Empoasca maligna, Empoasca solana, Empoasca stevensi, Eriosoma spp., z.B. Eriosoma americanum, Eriosoma lanigerum, Eriosoma pyricola, Erythroneura spp., Eucalyptolyma spp., Euphyllura spp., Euscelis bilobatus, Ferrisia spp., Geococcus coffeae, Glycaspis spp., Heteropsylla cubana, Heteropsylla spinulosa, Homalodisca coagulata, Hyalopterus arundinis, Hyalopterus pruni, Icerya spp., z.B. Icerya purchasi, Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., z.B. Lecanium corni (=Parthenolecanium corni), Lepidosaphes spp., z.B. Lepidosaphes ulmi, Lipaphis erysimi, Lycorma delicatula, Macrosiphum spp., z.B. Macrosiphum euphorbiae, Macrosiphum lilii, Macrosiphum rosae, Macrosteles facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metcalfa pruinosa, Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., z.B. Myzus ascalonicus, Myzus cerasi, Myzus ligustri, Myzus ornatus, Myzus persicae,. Myzus nicotianae, Nasonovia ribisnigri, Nephotettix spp., z.B. Nephotettix cincticeps,, Nephotettix nigropictus, Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., z.B. Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., z.B. Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Phenacoccus spp., z.B. Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., z.B. Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., z.B. Planococcus citri, Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., z.B. Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus viburni, Psyllopsis spp., Psylla spp., z.B. Psylla buxi, Psylla mali, Psylla pyri, Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., z.B. Quadraspidiotus juglansregiae, Quadraspidiotus ostreaeformis, Quadraspidiotus perniciosus, Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., z.B. Rhopalosiphum maidis, Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominale, Saissetia spp., z.B. Saissetia coffeae, Saissetia miranda, Saissetia neglecta, Saissetia oleae, Scaphoideus titanus, Schizaphis graminum, Selenaspidus articulatus, Sitobion avenae, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina, Siphoninus phillyreae, Tenalaphara malayensis,Tetragonocephela spp., Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., z.B. Toxoptera aurantii, Toxoptera citricidus, Trialeurodes vaporariorum, Trioza spp., z.B. Trioza diospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp.;
aus der Unterordnung der Heteroptera z.B. Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., z.B. Cimex adjunctus, Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., z.B. Euschistus heros, Euschistus servus, Euschistus tristigmus, Euschistus variolarius, Eurygaster spp., Halyomorpha halys, Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptocorisa varicornis, Leptoglossus occidentalis, Leptoglossus phyllopus, Lygocoris spp., z.B. Lygocoris pabulinus, Lygus spp., z.B. Lygus elisus, Lygus hesperus, Lygus lineolaris, Macropes excavatus, Monalonion atratum, Nezara spp., z.B. Nezara viridula, Oebalus spp., Piesma quadrata, Piezodorus spp., z.B. Piezodorus guildinii, Psallus spp., Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp.;
aus der Ordnung der Hymenoptera z.B. Acromyrmex spp., Athalia spp., z.B. Athalia rosae, Atta spp., Diprion spp., z.B. Diprion similis, Hoplocampa spp., z.B. Hoplocampa cookei, Hoplocampa testudinea, Lasius spp., Linepithema humile, Monomorium pharaonis, Sirex spp., Solenopsis invicta, Tapinoma spp., Urocerus spp., Vespa spp., z.B. Vespa crabro, Xeris spp.;
aus der Ordnung der Isopoda z.B. Armadillidium vulgare, Oniscus asellus, Porcellio scaber;
aus der Ordnung der Isoptera z.B. Coptotermes spp., z.B. Coptotermes formosanus, Cornitermes cumulans, Cryptotermes spp., Incisitermes spp., Microtermes obesi, Odontotermes spp., Reticulitermes spp., z.B. Reticulitermes flavipes, Reticulitermes hesperus;
aus der Ordnung der Lepidoptera z.B. Achroia grisella, Acronicta major, Adoxophyes spp., z.B. Adoxophyes orana, Aedia leucomelas, Agrotis spp., z.B. Agrotis segetum, Agrotis ipsilon, Alabama spp., z.B. Alabama argillacea, Amyelois transitella, Anarsia spp., Anticarsia spp., z.B. Anticarsia gemmatalis, Argyroploce spp., Barathra brassicae, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp., Caloptilia theivora, Capua reticulana, Carpocapsa pomonella, Carposina niponensis, Cheimatobia brumata, Chilo spp., z.B. Chilo plejadellus, Chilo suppressalis, Choristoneura spp., Clysia ambiguella, Cnaphalocerus spp., Cnaphalocrocis medinalis, Cnephasia spp., Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Cydia spp., z.B. Cydia nigricana, Cydia pomonella, Dalaca noctuides, Diaphania spp., Diatraea saccharalis, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eldana saccharina, Ephestia spp., z.B. Ephestia elutella, Ephestia kuehniella, Epinotia spp., Epiphyas postvittana, Etiella spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp., z.B. Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Gracillaria spp., Grapholitha spp., z.B. Grapholita molesta, Grapholita prunivora, Hedylepta spp., Helicoverpa spp., z.B. Helicoverpa armigera, Helicoverpa zea, Heliothis spp., z.B. Heliothis virescens Hofmannophila pseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padella, Kakivoria flavofasciata, Laphygma spp., Leucinodes orbonalis, Leucoptera spp., z.B. Leucoptera coffeella, Lithocolletis spp., z.B. Lithocolletis blancardella, Lithophane antennata, Lobesia spp., z.B. Lobesia botrana, Loxagrotis albicosta, Lymantria spp., z.b. Lymantria dispar, Lyonetia spp., z.B. Lyonetia clerkella, Malacosoma neustria, Maruca testulalis, Mamestra brassicae, Melanitis leda, Mocis spp., Monopis obviella, Mythimna separata, Nemapogon cloacellus, Nymphula spp., Oiketicus spp., Oria spp., Orthaga spp., Ostrinia spp., z.B. Ostrinia nubilalis, Oulema melanopus, Oulema oryzae, Panolis flammea, Parnara spp., Pectinophora spp., z.B. Pectinophora gossypiella, Perileucoptera spp., Phthorimaea spp., z.B. Phthorimaea operculella, Phyllocnistis citrella, Phyllonorycter spp., z.B. Phyllonorycter blancardella, Phyllonorycter crataegella, Pieris spp., z.B. Pieris rapae, Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylostella (=Plutella maculipennis), Prays spp., Prodenia spp., Protoparce spp., Pseudaletia spp., z.B. Pseudaletia unipuncta, Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., z.B. Schoenobius bipunctifer, Scirpophaga spp., z.B. Scirpophaga innotata, Scotia segetum, Sesamia spp., z.B. Sesamia inferens, Sparganothis spp., Spodoptera spp., z.b. Spodoptera eradiana, Spodoptera exigua, Spodoptera frugiperda, Spodoptera praefica, Stathmopoda spp., Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora, Thermesia gemmatalis, Tinea cloacella, Tinea pellionella, Tineola bisselliella, Tortrix spp., Trichophaga tapetzella, Trichoplusia spp., z.B. Trichoplusia ni, Tryporyza incertulas, Tuta absoluta, Virachola spp.;
aus der Ordnung der Orthoptera oder Saltatoria z.B. Acheta domesticus, Dichroplus spp., Gryllotalpa spp., z.B. Gryllotalpa gryllotalpa, Hieroglyphus spp., Locusta spp., z.B. Locusta migratoria, Melanoplus spp., z.B. Melanoplus devastator, Paratlanticus ussuriensis, Schistocerca gregaria;
aus der Ordnung der Phthiraptera z.B. Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxera vastatrix, Phthirus pubis, Trichodectes spp.;
aus der Ordnung der Psocoptera z.B. Lepinotus spp., Liposcelis spp.;
aus der Ordnung der Siphonaptera z.B. Ceratophyllus spp., Ctenocephalides spp., z.B. Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis;
aus der Ordnung der Thysanoptera z.B. Anaphothrips obscurus, Baliothrips biformis, Drepanothrips reuteri, Enneothrips flavens, Frankliniella spp., z.B. Frankliniella fusca, Frankliniella occidentalis, Frankliniella schultzei, Frankliniella tritici, Frankliniella vaccinii, Frankliniella williamsi, Heliothrips spp., Hercinothrips femoralis, Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamomi, Thrips spp., z.B. Thrips palmi, Thrips tabaci;
aus der Ordnung der Zygentoma (= Thysanura), z. B. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica;
aus der Klasse der Symphyla z.B. Scutigerella spp., z.B. Scutigerella immaculata;
Schädlinge aus dem Stamm der Mollusca, insbesondere aus der Klasse der Bivalvia, z.B. Dreissena spp.;
sowie aus der Klasse der Gastropoda z.B. Arion spp., z.B. Arion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., z.B. Deroceras laeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp.;
Tier- und Humanparasiten aus den Stämmen der Platyhelminthes und Nematoda, z.B. Aelurostrongylus spp., Amidostomum spp., Ancylostoma spp, Angiostrongylus spp., Anisakis spp., Anoplocephala spp., Ascaris spp., Ascaridia spp., Baylisascaris spp., Brugia spp., Bunostomum spp., Capillaria spp., Chabertia spp., Clonorchis spp., Cooperia spp., Crenosoma spp., Cyathostoma spp., Dicrocoelium spp., Dictyocaulus spp., Diphyllobothrium spp., Dipylidium spp., Dirofilaria spp., Dracunculus spp., Echinococcus spp., Echinostoma spp., Enterobius spp., Eucoleus spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Filaroides spp., Gongylonema spp., Gyrodactylus spp., Habronema spp., Haemonchus spp., Heligmosomoides spp., Heterakis spp., Hymenolepis spp., Hyostrongylus spp., Litomosoides spp., Loa spp., Metastrongylus spp., Metorchis spp., Mesocestoides spp., Moniezia spp., Muellerius spp., Necator spp., Nematodirus spp., Nippostrongylus spp., Oesophagostomum spp., Ollulanus spp., Onchocerca spp, Opisthorchis spp., Oslerus spp., Ostertagia spp., Oxyuris spp., Paracapillaria spp., Parafilaria spp., Paragonimus spp., Paramphistomum spp., Paranoplocephala spp., Parascaris spp., Passalurus spp., Protostrongylus spp., Schistosoma spp., Setaria spp., Spirocerca spp., Stephanofilaria spp., Stephanurus spp., Strongyloides spp., Strongylus spp., Syngamus spp., Taenia spp., Teladorsagia spp., Thelazia spp., Toxascaris spp., Toxocara spp., Trichinella spp., Trichobilharzia spp., Trichostrongylus spp., Trichuris spp., Uncinaria spp., Wuchereria spp.;
Pflanzenschädlinge aus dem Stamm der Nematoda, d.h. pflanzenparasitäre Nematoden, insbesondere Aglenchus spp., z.B. Aglenchus agricola, Anguina spp., z.B. Anguina tritici, Aphelenchoides spp., z.B. Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimus spp., z.B. Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus spp., z.B. Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp., z.B. Cacopaurus pestis, Criconemella spp., z.B. Criconemella curvata, Criconemella onoensis, Criconemella ornata, Criconemella rusium, Criconemella xenoplax (= Mesocriconema xenoplax), Criconemoides spp., z.B. Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum, Ditylenchus spp., z.B. Ditylenchus dipsaci, Dolichodorus spp., Globodera spp., z.B. Globodera pallida, Globodera rostochiensis, Helicotylenchus spp., z.B. Helicotylenchus dihystera, Hemicriconemoides spp., Hemicycliophora spp., Heterodera spp., z.B. Heterodera avenae, Heterodera glycines, Heterodera schachtii, Hoplolaimus spp., Longidorus spp., z.B. Longidorus africanus, Meloidogyne spp., z.B. Meloidogyne chitwoodi, Meloidogyne fallax, Meloidogyne hapla, Meloidogyne incognita, Meloinema spp., Nacobbus spp., Neotylenchus spp., Paraphelenchus spp., Paratrichodorus spp., z.B. Paratrichodorus minor, Pratylenchus spp., z.B. Pratylenchus penetrans, Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp., z.B. Radopholus citrophilus, Radopholus similis, Rotylenchulus spp., Rotylenchus spp., Scutellonema spp., Subanguina spp., Trichodorus spp., z.B. Trichodorus obtusus, Trichodorus primitivus, Tylenchorhynchus spp., z.B. Tylenchorhynchus annulatus, Tylenchulus spp., z.B. Tylenchulus semipenetrans, Xiphinema spp., z.B. Xiphinema index.The compounds of the formula (I) are suitable for plant protection, favorable warm-blooded toxicity and good environmental compatibility for the protection of plants and plant organs from biotic and abiotic stress factors, for increasing crop yields, improving the quality of the crop and for controlling animal pests, in particular insects, Arachnids, helminths, nematodes and molluscs found in agriculture, horticulture, livestock, aquaculture, forestry, gardens and recreation, storage and materials protection and hygiene. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development. The above mentioned pests include:
Pests of the genus Arthropoda, in particular of the class Arachnida eg Acarus spp., Eg Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., Eg Aculus fockeui, Aculus badendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., Eg Brevipalpus phoenicis, Bryobia graminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp., Eg Eotetranychus hicoriae , Epitrimerus pyri, Eutetranychus spp., Eg Eutetranychus banksi, Eriophyes spp., Eg Eriophyes pyri, Glycyphagus domesticus, Halotydeus destructor, Hemitarsonemus spp., Eg Hemitarsonemus latus (= Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp., Latrodectus spp. , Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp., Oligonychus spp., Eg Oligonychus coniferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychus pra tensis, Oligonychus punicae, Oligonychus yothersi, Ornithodorus spp., Ornithonyssus spp., Panonychus spp., eg Panonychus citri (= Metatetranychus citri), Panonychus ulmi (= Metatetranychus ulmi), Phyllocoptruta oleivora, Platytetranychus multidigituli, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemus spp., Steneotarsonemus spinki, Tarsonemus spp., Eg Tarsonemus confusus, Tarsonemus pallidus, Tetranychus spp., Eg Tetranychus cinnabaris, Tetranychus turkestani, Tetranychus urticae, Trombicula alfreddugesi, Vaejovis spp., Vasates lycopersici;
from the genus of Chilopoda, for example Geophilus spp., Scutigera spp .;
from the order or class of Collembola eg Onychiurus armatus; Sminthurus viridis;
from the class Diplopoda eg Blaniulus guttulatus;
from the class of the Insecta, eg from the order of the Blattodea eg Blatta orientalis, Blattella asahinai, Blattella germanica, Leucophaea maderae, Panchlora spp., Parcoblatta spp., Periplaneta spp., eg Periplaneta americana, Periplaneta australasiae, Supella longipalpa;
from the order of the Coleoptera eg Acalymma vittatum, Acanthoscelides obtectus, Adoretus spp., Agelastica alni, Agriotes spp., eg Agriotes linneatus, Agriotes mancus, Alphitobius diaperinus, Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., Anthonomus spp., eg Anthonomus grandis , Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp., Eg Atomaria linearis, Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp., Eg Bruchus pisorum, Bruchus rufimanus, Cassida spp., Cerotoma trifurcata, Ceutorrhynchus eg Ceutorrhynchus assimilis, Ceutorrhynchus quadridens, Ceutorrhynchus rapae, Chaetocnema spp., eg Chaetocnema confinis, Chaetocnema denticulata, Chaetocnema ectypa, Cleonus mendicus, Conoderus spp., Cosmopolites spp., eg Cosmopolites sordidus, Costelytra zealandica, Ctenicera spp., Curculio spp., eg Curculio caryae, Curculio caryatrypes, Curculio obtusus, Curculio sayi, Cryptolestes ferrugineus, Cryptolestes pusillus, Cryptorhynchus lapathi, Cryptorhynchus mangiferae, Cylindrocopturus spp., Cylindrocopturus adspersus, Cylindrocopturus furnissi, Dermestes spp., Diabrotica spp., eg Diabrotica balteata, Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp., Dicladispa armigera, Diloboderus spp., Epilachna spp., Eg Epilachna borealis, Epilachna varivestis, Epitrix spp., Eg Epitrix cucumeris, Epitrix fuscula, Epitrix hirtipennis, Epitrix subcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides, Gnathocerus cornutus, Hellula and alis, Heteronychus arator , Heteronyx spp., Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypomeces squamosus, Hypothenemus spp., Eg Hypothenemus hampei, Hypothenemus obscurus, Hypothenemus pubescens, Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsa decemlineata , Leucoptera spp., Eg Leucoptera coffeella, Lissorhoptrus oryzop hilus, Lixus spp., Luperomorpha xanthodera, Luperodes spp., Lyctus spp., Megascelis spp., Melanotus spp., eg Melanotus longulus oregonensis, Meligethes aeneus, Melolontha spp., eg Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, oryzae Oryzaphagus, Otiorhynchus spp., for example, Otiorhynchus cribricollis, Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Phyllophaga helleri Phyllotreta spp., Eg Phyllotreta armoraciae, Phyllotreta pusilla, Phyllotreta ramosa, Phyllotreta striolata, Popillia japonica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp., Eg Psylliodes affinis, Psylliodes chrysocephala, Psylliodes punctulata, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp., eg Sitophilus granarius, Sitophilus linearis, Sitophilus oryzae, Sitophilus zeam ais, Sphenophorus spp., Stegobium paniceum, Staphylococcus spp., eg, Starchus paludatus, Symphyletes spp., Tanymecus spp., eg, Tanymecus dilaticollis, Tanymecus indicus, Tanymecus palliatus, Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp., eg, Tribolium audax, Tribolium castaneum, Tribolium confusum, Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., eg Zabrus tenebrioides;
from the order of the Diptera eg Aedes spp., eg Aedes aegypti, Aedes albopictus, Aedes sticticus, Aedes vexans, Agromyza spp., eg Agromyza frontella, Agromyza parvicornis, Anastrepha spp., Anopheles spp., eg Anopheles quadrimaculatus, Anopheles gambiae, Asphondylia spp., Bactrocera spp., eg Bactrocera cucurbitae, Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata, Chironomus spp., Chrysomya spp., Chrysops spp., Chrysozona pluvialis, Cochliomya spp., Contarinia spp Contarinia johnsoni, Contarina nasturtii, Contarinia pyrivora, Contarinia schulzi, Contarina sorghicola, Contarinia tritici, Cordylobia anthropophaga, Cricotopus sylvestris, Culex spp., eg Culex pipiens, Culex quinquefasciatus, Culicoides spp., Culiseta spp., Cuterebra spp. Dacus oleae, Dasineura spp., Eg, Dasineura brassicae, Delia spp., Eg Delia antiqua, Delia coarctata, Delia florilega, Delia platura, Delia radicum, Dermatobia hominis, Drosophila sp p., eg, Drosophila melanogaster, Drosophila suzukii, Echinocnemus spp., Fannia spp., Gasterophilus spp., Glossina spp., Haematopota spp., Hydrellia spp., Hydrellia griseola, Hylemya spp., Hippobosca spp., Hypoderma spp., Liriomyza spp., eg Liriomyza brassicae, Liriomyza huidobrensis, Liriomyza sativae, Lucilia spp., eg Lucilia cuprina, Lutzomyia spp., Mansonia spp., Musca spp., eg Musca domestica, Musca domestica vicina, Oestrus spp., Oscinella frit, Paratanytarsus spp , Paralauterborniella subcincta, Pegomya spp., Eg Pegomya betae, Pegomya hyoscyami, Pegomya rubivora, Phlebotomus spp., Phorbia spp., Phormia spp., Piophila casei, Prodiplosis spp., Psila rosae, Rhagoletis spp., Eg Rhagoletis cingulata, Rhagoletis completa, Rhagoletis fausta, Rhagoletis indifferens, Rhagoletis mendax, Rhagoletis pomonella, Sarcophaga spp., Simulium spp., eg Simulium meridionale, Stomoxys spp., Tabanus spp., Tetanops spp., Tipula spp., eg Tipula paludosa, Tipula simplex;
from the order of the Hemiptera eg Acizzia acaciaebaileyanae, Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosipon spp., eg Acyrthosiphon pisum, Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleyrodes proletella, Aleurolobus barodensis, Aleurothrixus floccosus, Allocaridara malayensis, Amrasca spp., Eg Amrasca bigutulla, Amrasca devastans, Anuraphis cardui, Aonidiella spp., Eg Aonidiella aurantii, Aonidiella citrina, Aonidiella inornata, Aphanostigma piri, Aphis spp., Eg Aphis citricola, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis glycines , Aphis gossypii, Aphis hederae, Aphis illinoisensis, Aphis middletoni, Aphis nasturtii, Aphis nerii, Aphis pomi, Aphis spiraecola, Aphis viburniphila, Arboridia apicalis, Arytainilla spp., Aspidiella spp., Aspidiotus spp., Eg Aspidiotus nerii, Atanus spp. , Aulacorthum solani, Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae, Brachycaudus helichrysi, Brachycolus spp., Brevicoryne brassicae, Cacopsylla spp. , eg Cacopsylla pyricola, Calligypona marginata, Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chondracris rosea, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp., Eg Coccus hesperidum, Coccus longulus, Coccus pseudomagnoliarum, Coccus viridis, Cryptomyzus ribis, Cryptoneossa spp., Ctenarytaina spp., Dalbulus spp., Dialeurodes citri, Diaphorina citri, Diaspis spp., Drosicha spp., Dysaphis spp., Eg Dysaphis apiifolia, Dysaphis plantaginea, Dysaphis tulipae, Dysmicoccus spp., Empoasca spp., Eg Empoasca abrupta, Empoasca fabae, Empoasca maligna, Empoasca solana, Empoasca stevensi, Eriosoma spp., Euphyllura spp., Euscelis bilobatus, Ferrisia spp., Geococcus coffeae, Glycaspis spp., Heteropsylla cubana, Heteropsylla spinulosa, Homalodisca coagulata, Hyalopterus arundinis , Hyalopterus pruni, Icerya spp., Eg Icerya purchasi, Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Eg Lecanium corni (= Parthenolecanium corni), Lepidosaphes spp., Eg Lepidosaphes ulmi, Lipaphis erysimi, Lycorma delicatula, Macrosiphum spp., Eg Macrosiphum euphorbiae, Macrosiphum lilii, Macrosiphum rosae, Macrosteles facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metcalfa pruinosa, Metopolophium dirhodum, Monellia costalis , Monzusopsis pecanis, Myzus spp., Eg Myzus ascalonicus, Myzus cerasi, Myzus ligustri, Myzus ornatus, Myzus persicae ,. Myzus nicotianae, Nasonovia ribisnigri, Nephotettix spp., Eg Nephotettix cincticeps, Nephotettix nigropictus, Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., Eg Paratrioza cockerelli, Parlatoria spp. Pemphigus spp., Eg Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Phenacoccus spp., Eg Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., Eg Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., Eg Planococcus citri, Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Eg Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus viburni, Psyllopsis spp., Psylla spp., Eg Psylla buxi, Psylla mali, Psylla pyri, Pteromalus spp. , Pyrilla spp., Quadraspidiotus spp., Eg, Quadraspidiotus juglansregiae, Quadraspidiotus ostreaeformis, Quadr aspidiotus perniciosus, Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., eg Rhopalosiphum maidis, Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominal, Saissetia spp., eg Saissetia coffeae, Saissetia miranda, Saissetia neglecta, Saissetia oleae, Scaphoideus titanus, Schizaphis graminum, Selenaspidus articulatus, Sitobion avenae, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina, Siphoninus phillyreae, Tenalaphara malayensis, Tetragonocephela spp., Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., Eg Toxoptera aurantii, Toxoptera citricidus, Trialeurodes vaporariorum , Trioza spp., Eg Trioza diospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp .;
from the suborder of the Heteroptera eg Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., eg Cimex adjunctus, Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., eg Eushtistus heros, Euschistus servus, Eustistus tristigmus, Euschistus variolarius, Eurygaster spp., Halyomorpha halys, Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptocorisa varicornis, Leptoglossus occidentalis, Leptoglossus phyllopus, Lygocoris spp., Eg Lygocoris pabulinus, Lygus spp., Eg Lygus elisus, Lygus hesperus, Lygus lineolaris, Macropes excavatus, Monalonion atratum, Nezara spp., eg Nezara viridula, Oebalus spp., Piesma quadrata, Piezodorus spp., eg Piezodorus guildinii, Psallus spp., Pseudacysta persea, Rhodnius spp., Sahlbergella singularis , Scaptocoris castanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp .;
from the order of the Hymenoptera eg Acromyrmex spp., Athalia spp., eg Athalia rosae, Atta spp., Diprion spp., eg Diprion similis, Hoplocampa spp., eg Hoplocampa cookei, Hoplocampa testudinea, Lasius spp., Linepithema humile, Monomorium pharaonis , Sirex spp., Solenopsis invicta, Tapinoma spp., Urocerus spp., Vespa spp., Eg Vespa crabro, Xeris spp .;
from the order of Isopoda, for example, Armadillidium vulgare, Oniscus asellus, Porcellio scaber;
from the order of the Isoptera eg Coptotermes spp., eg Coptotermes formosanus, Cornitermes cumulans, Cryptotermes spp., Incisitermes spp., Microtermes obesi, Odontotermes spp., Reticulitermes spp., eg Reticulitermes flavipes, Reticulitermes hesperus;
from the order of the Lepidoptera eg Achroia grisella, Acronica major, Adoxophyes spp., eg Adoxophyes orana, Aedia leucomelas, Agrotis spp., eg Agrotis segetum, Agrotis ipsilon, Alabama spp., eg Alabama argillacea, Amyelois transitella, Anarsia spp., Anticarsia spp., eg Anticarsia gemmatalis, Argyroploce spp., Barathra brassicae, Borbo cinnara, Bucculatrix thurberiella, Bupalus pinarius, Busseola spp., Cacoecia spp., Caloptilia theivora, Capua reticulana, Carpocapsa pomonella, Carposina niponensis, Cheimatobia brumata, Chilo spp. eg Chilo plejadellus, Chilo suppressalis, Choristoneura spp., Clysia ambiguella, Cnaphalocerus spp., Cnaphalocrocis medinalis, Cnephasia spp., Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Cydia spp., eg Cydia nigricana, Cydia pomonella, Dalaca noctuides , Diaphania spp., Diatraea saccharalis, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eldana saccharina, Ephestia spp., Eg Ephestia elutella, Ephestia kuehniella, Epinotia spp., Epiph yas postvittana, Etiella spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp., eg Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Gracillaria spp., Grapholitha spp., eg Grapholita molesta, Grapholita prunivora, Hedylepta spp Helicoverpa spp., Eg Helicoverpa armigera, Helicoverpa zea, Heliothis spp., Eg Heliothis virescens Hofmannophila pseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padella, Kakivoria flavofasciata, Laphygma spp., Leucinodes orbonalis, Leucoptera spp., Eg Leucoptera coffeella, Lithocolletis spp., eg Lithocolletis blancardella, Lithophane antennata, Lobesia spp., eg Lobesia botrana, Loxagrotis albicosta, Lymantria spp., eg Lymantria dispar, Lyonetia spp., eg Lyonetia clerkella, Malacosoma neustria, Maruca testulalis, Mamestra brassicae, Melanitis leda, Mocis spp., Monopis obviella, Mythimna separata, Nemapogon cloacellus, Nymphula spp., Oiketicus spp., Oria spp., Orthaga spp., Ostrinia spp., eg Ostrinia nubilalis, Oulema melanopus, Oulema oryzae, Panolis flammea, Parnara spp., Pectinophora spp., Eg Pectinophora gossypiella, Perileucoptera spp., Phthorimaea spp., Eg Phthorimaea operculella, Phyllocnistis citrella, Phyllonorycter spp., Eg Phyllonorycter blancardella, Phyllonorycter crataegella, Pieris spp., Eg Pieris rapae, Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylostella (= Plutella maculipennis), Prays spp., Prodenia spp., Protoparce spp., Pseudaletia spp., Eg Pseudaletia unipuncta, Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., eg Schoenobius bipunctifer, Scirpophaga spp., eg Scirpophaga innotata, Scotia segetum, Sesamia spp., eg Sesamia inferens, Sparganothis spp., Spodoptera spp., eg Spodoptera eradiana, Spodoptera exigua, Spodoptera frugiperda, Spodoptera praefica, Stathmopoda spp., Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora, Thermesia gemmatalis, Tinea cloacella, Tinea pellionella, Tineola bissell iella, Tortrix spp., Trichophaga tapetzella, Trichoplusia spp., eg Trichoplusia ni, Tryporyza incertulas, Tuta absoluta, Virachola spp .;
from the order of Orthoptera or Saltatoria eg Acheta domesticus, Dichroplus spp., Gryllotalpa spp., eg Gryllotalpa gryllotalpa, Hieroglyphus spp., Locusta spp., eg Locusta migratoria, Melanoplus spp., eg Melanoplus devastator, Paratlanticus ussuriensis, Schistocerca gregaria;
from the order of Phthiraptera eg Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxera vastatrix, Phthirus pubis, Trichodectes spp .;
from the order of Psocoptera eg Lepinotus spp., Liposcelis spp .;
from the order of Siphonaptera eg Ceratophyllus spp., Ctenocephalides spp., eg Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis;
from the order of the Thysanoptera eg Anaphothrips obscurus, Baliothrips biformis, Drepanothrips reuteri, Enneothrips flavens, Frankliniella spp., eg Frankliniella fusca, Frankliniella occidentalis, Frankliniella schultzei, Frankliniella tritici, Frankliniella vaccinii, Frankliniella williamsi, Heliothrips spp., Hercinothrips femoralis, Rhipiphorothrips cruentatus , Scirtothrips spp., Taeniothrips cardamomi, Thrips spp., Eg Thrips palmi, Thrips tabaci;
from the order of Zygentoma (= Thysanura), z. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica;
from the class of Symphyla eg Scutigerella spp., eg Scutigerella immaculata;
Pests from the strain of Mollusca, in particular from the class of bivalvia, for example Dreissena spp .;
and from the class of Gastropoda eg Arion spp., eg Arion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., eg Deroceras laeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp .
Animal and human parasites from the strains of Platyhelminthes and Nematoda, eg Aelurostrongylus spp., Amidostomum spp., Ancylostoma spp, Angiostrongylus spp., Anisakis spp., Anoplocephala spp., Ascaris spp., Ascaridia spp., Baylisascaris spp., Brugia spp , Bunostomum spp., Capillaria spp., Chabertia spp., Clonorchis spp., Cooperia spp., Crenosoma spp., Cyathostoma spp., Dicrocoelium spp., Dictyocaulus spp., Diphyllobothrium spp., Dipylidium spp., Dirofilaria spp. Dracunculus spp., Echinococcus spp., Echinostoma spp., Enterobius spp., Eucoleus spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Filaroides spp., Gongylonema spp., Gyrodactylus spp., Habronema spp., Haemonchus spp , Heligmosomoides spp., Heterakis spp., Hymenolepis spp., Hyostrongylus spp., Litomosoides spp., Loa spp., Metastrongylus spp., Metorchis spp., Mesocestoides spp., Moniezia spp., Muellerius spp., Necator spp. Nematodirus spp., Nippostrongylus spp., Oesophagostomum spp., Ollulanus spp., Onchocerca spp, Op isthorchis spp., Oslerus spp., Ostertagia spp., Oxyuris spp., Paracapillaria spp., Parafilaria spp., Paragonimus spp., Paramphistomum spp., Paranoplocephala spp., Parascaris spp., Passalurus spp., Protostrongylus spp., Schistosoma spp , Setaria spp., Spirocerca spp., Stephanofilaria spp., Stephanurus spp., Strongyloides spp., Strongylus spp., Syngamus spp., Taenia spp., Teladorsagia spp., Thelazia spp., Toxascaris spp., Toxocara spp. Trichinella spp., Trichobilharzia spp., Trichostrongylus spp., Trichuris spp., Uncinaria spp., Wuchereria spp .;
Plant pests from the Nematoda strain, ie plant parasitic nematodes, in particular Aglenchus spp., Eg Aglenchus agricola, Anguina spp., Eg Anguina tritici, Aphelenchoides spp., Eg Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimus spp., Eg Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus spp., Eg Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp., Eg Cacopaurus pestis, Criconemella spp., Eg Criconemella curvata, Criconemella onoensis, Criconemella ornata, Criconemella rusium, Criconemella xenoplax (= Mesocriconema xenoplax), Criconemoides spp., Eg Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum, Ditylenchus spp., Eg Ditylenchus dipsaci, Dolichodorus spp., Globodera spp., Eg Globodera pallida, Globodera rostochiensis, Helicotylenchus spp., Eg Helicotylenchus dihystera, Hemicriconemoides spp., Hemicycliophora spp., Heterodera spp., eg Heterodera avenae, Heter ora glycines, Heterodera schachtii, Hoplolaimus spp., Longidorus spp., eg Longidorus africanus, Meloidogyne spp., eg Meloidogyne chitwoodi, Meloidogyne fallax, Meloidogyne hapla, Meloidogyne incognita, Meloinema spp., Nacobbus spp., Neotylenchus spp., Paraphelenchus spp. , Paratrichodorus spp., Eg Paratrichodorus minor, Pratylenchus spp., Eg Pratylenchus penetrans, Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp., Eg Radopholus citrophilus, Radopholus similis, Rotylenchulus spp., Rotylenchus spp , Scutellonema spp., Subanguina spp., Trichodorus spp., Eg Trichodorus obtusus, Trichodorus primitivus, Tylenchorhynchus spp., Eg Tylenchorhynchus annulatus, Tylenchulus spp., Eg Tylenchulus semipenetrans, Xiphinema spp., Eg Xiphinema index.

Weiterhin lässt sich aus dem Unterreich der Protozoa die Ordnung der Coccidia z.B. Eimeria spp. bekämpfen.Furthermore, the order of the coccidia, eg Eimeria spp., Can be determined from the sub-region of the protozoa. fight.

Die Verbindungen der Formel (I) können gegebenenfalls in bestimmten Konzentrationen bzw. Aufwandmengen auch als Herbizide, Safener, Wachstumsregulatoren oder Mittel zur Verbesserung der Pflanzeneigenschaften, als Mikrobizide oder Gametozide, beispielsweise als Fungizide, Antimykotika, Bakterizide, Virizide (einschließlich Mittel gegen Viroide) oder als Mittel gegen MLO (Mycoplasmalike-organism) und RLO (Rickettsia-like-organism) verwendet werden. Sie lassen sich gegebenenfalls auch als Zwischen- oder Vorprodukte für die Synthese weiterer Wirkstoffe einsetzen.The compounds of the formula (I) may optionally also be used in certain concentrations or application rates as herbicides, safeners, growth regulators or agents for improving plant properties, as microbicides or gametocides, for example as fungicides, antimycotics, bactericides, viricides (including anti-viral agents) or as a remedy for MLO (Mycoplasmalike organism) and RLO (Rickettsia-like-organism). If appropriate, they can also be used as intermediates or precursors for the synthesis of further active ingredients.

Formulierungenformulations

Die vorliegende Erfindung betrifft weiterhin Formulierungen und daraus bereitete Anwendungsformen als Schädlingsbekämpfungsmittel wie z. B. Drench-, Drip- und Spritzbrühen, umfassend mindestens eine Verbindung der Formel (I). Gegebenenfalls enthalten die Anwendungsformen weitere Schädlingsbekämpfungsmittel und/oder die Wirkung verbessernde Adjuvantien wie Penetrationsförderer, z. B. vegetative Öle wie beispielsweise Rapsöl, Sonnenblumenöl, Mineralöle wie beispielsweise Paraffinöle, Alkylester vegetativer Fettsäuren wie beispielsweise Rapsöl- oder Sojaölmethylester oder Alkanol-alkoxylate und/oder Spreitmittel wie beispielsweise Alkylsiloxane und/oder Salze z.B. organische oder anorganische Ammonium- oder Phosphoniumsalze wie beispielsweise Ammoniumsulfat oder Diammonium-hydrogenphosphat und/oder die Retention fördernde Mittel wie z. B. Dioctylsulfosuccinat oder Hydroxypropyl-guar Polymere und/oder Humectants wie z.B. Glycerin und/oder Dünger wie beispielsweise Ammonium-, Kalium- oder Phosphor-enthaltende Dünger.The present invention further relates to formulations and application forms prepared therefrom as pesticides such. B. drench, drip and spray liquors, comprising at least one compound of formula (I). Optionally, the uses include other pesticides and / or effect-improving adjuvants such as penetration enhancers, e.g. For example, vegetative oils such as rapeseed oil, sunflower oil, mineral oils such as paraffin oils, alkyl esters of vegetal fatty acids such as rapeseed oil or soybean oil methyl ester or alkanol alkoxylates and / or spreading agents such as alkyl siloxanes and / or salts, e.g. organic or inorganic ammonium or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate and / or retention-promoting agents such. Dioctylsulfosuccinate or hydroxypropyl-guar polymers and / or humectants, e.g. Glycerol and / or fertilizers such as ammonium, potassium or phosphorus-containing fertilizer.

Übliche Formulierungen sind beispielsweise wasserlösliche Flüssigkeiten (SL), Emulsionskonzentrate (EC), Emulsionen in Wasser (EW), Suspensionskonzentrate (SC, SE, FS, OD), in Wasser dispergierbare Granulate (WG), Granulate (GR) und Kapselkonzentrate (CS); diese und weitere mögliche Formuliertypen sind beispielsweise durch Crop Life International und in Pesticide Specifications, Manual on development and use of FAO and WHO specifications for pesticides, FAO Plant Production and Protection Papers - 173, prepared by the FAO/WHO Joint Meeting on Pesticide Specifications, 2004, ISBN: 9251048576 beschrieben. Gegebenenfalls enthalten die Formulierungen neben einem oder mehreren Verbindungen der Formel (I) weitere agrochemische Wirkstoffe.Typical formulations are, for example, water-soluble liquids (SL), emulsion concentrates (EC), emulsions in water (EW), suspension concentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR) and capsule concentrates (CS). ; These and other possible formulation types are, for example, by Crop Life International and in Pesticide Specifications, Manual on Development and Use of FAO and WHO Specifications for Pesticides, FAO Plant Production and Protection Papers - 173, prepared by the FAO / WHO Joint Meeting on Pesticide Specifications, 2004, ISBN: 9251048576 described. If appropriate, the formulations contain, in addition to one or more compounds of the formula (I), further agrochemical active substances.

Vorzugsweise handelt es sich um Formulierungen oder Anwendungsformen, welche Hilfsstoffe wie beispielsweise Streckmittel, Lösemittel, Spontanitätsförderer, Trägerstoffe, Emulgiermittel, Dispergiermittel, Frostschutzmittel, Biozide, Verdicker und/oder weitere Hilfsstoffe wie beispielsweise Adjuvantien enthalten. Ein Adjuvant in diesem Kontext ist eine Komponente, die die biologische Wirkung der Formulierung verbessert, ohne dass die Komponente selbst eine biologische Wirkung hat. Beispiele für Adjuvantien sind Mittel, die die Retention, das Spreitverhalten, das Anhaften an der Blattoberfläche oder die Penetration fördern.They are preferably formulations or use forms which contain auxiliaries, such as extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, antifreeze agents, biocides, thickeners and / or further auxiliaries, for example adjuvants. An adjuvant in this context is a component that enhances the biological effect of the formulation without the component itself having a biological effect. Examples of adjuvants are agents that promote retention, spreading behavior, adherence to the leaf surface, or penetration.

Diese Formulierungen werden in bekannter Weise hergestellt, z.B. durch Vermischen der Verbindungen der Formel (I) mit Hilfsstoffen wie beispielsweise Streckmitteln, Lösemitteln und/oder festen Trägerstoffen und/oder weiteren Hilfsstoffen wie beispielsweise oberflächenaktive Stoffe. Die Herstellung der Formulierungen erfolgt entweder in geeigneten Anlagen oder auch vor oder während der Anwendung.These formulations are prepared in a known manner, e.g. by mixing the compounds of the formula (I) with auxiliaries, such as, for example, extenders, solvents and / or solid carriers and / or further auxiliaries, for example surface-active substances. The preparation of the formulations is carried out either in suitable systems or before or during use.

Als Hilfsstoffe können solche Stoffe Verwendung finden, die geeignet sind, der Formulierung der Verbindungen der Formel (I) oder den aus diesen Formulierungen bereiteten Anwendungsformen (wie z.B. gebrauchsfähigen Schädlingsbekämpfungsmitteln wie Spritzbrühen oder Saatgutbeizen) besondere Eigenschaften, wie bestimmte physikalische, technische und/oder biologische Eigenschaften zu verleihen.Excipients which can be used are those which are suitable for the formulation of the compounds of the formula (I) or the use forms prepared from these formulations (such as, for example, ready-to-use pesticides such as spray liquors or seed dressings), such as certain physical, technical and / or biological properties To give properties.

Als Streckmittel eignen sich z.B. Wasser, polare und unpolare organische chemische Flüssigkeiten z.B. aus den Klassen der aromatischen und nicht-aromatischen Kohlenwasserstoffe (wie Paraffine, Alkylbenzole, Alkylnaphthaline, Chlorbenzole), der Alkohole und Polyole (die ggf. auch substituiert, verethert und/oder verestert sein können), der Ketone (wie Aceton, Cyclohexanon), Ester (auch Fette und Öle) und (Poly-)Ether, der einfachen und substituierten Amine, Amide, Lactame (wie N-Alkylpyrrolidone) und Lactone, der Sulfone und Sulfoxide (wie Dimethylsulfoxid).As extender, e.g. Water, polar and non-polar organic chemical liquids e.g. from the classes of aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also be substituted, etherified and / or esterified), ketones (such as acetone, cyclohexanone), Esters (including fats and oils) and (poly) ethers, simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethylsulfoxide).

Im Falle der Benutzung von Wasser als Streckmittel können z.B. auch organische Lösemittel als Hilfslösemittel verwendet werden. Als flüssige Lösemittel kommen im Wesentlichen infrage: Aromaten wie Xylol, Toluol oder Alkylnaphthaline, chlorierte Aromaten oder chlorierte aliphatische Kohlenwasser-stoffe wie Chlorbenzole, Chlorethylene oder Methylenchlorid, aliphatische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, z.B. Erdölfraktionen, mineralische und pflanzliche Öle, Alkohole wie Butanol oder Glykol sowie deren Ether und Ester, Ketone wie Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösemittel wie Dimethylformamid und Dimethylsulfoxid sowie Wasser.In the case of using water as an extender, e.g. also organic solvents can be used as auxiliary solvents. Suitable liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.

Grundsätzlich können alle geeigneten Lösemittel verwendet werden. Geeignete Lösemittel sind beispielsweise aromatische Kohlenwasserstoffe wie z.B. Xylol, Toluol oder Alkylnaphthaline, chlorierte aromatische oder aliphatische Kohlenwasserstoffe wie z.B. Chlorbenzol, Chlorethylen, oder Methylenchlorid, aliphatische Kohlenwasserstoffe wie z.B. Cyclohexan, Paraffine, Erdölfraktionen, mineralische und pflanzliche Öle, Alkohole wie z.B. Methanol, Ethanol, iso-Propanol, Butanol oder Glykol sowie deren Ether und Ester, Ketone wie z.B. Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösemittel wie Dimethylsulfoxid sowie Wasser.In principle, all suitable solvents can be used. Suitable solvents are, for example, aromatic hydrocarbons, e.g. Xylene, toluene or alkylnaphthalenes, chlorinated aromatic or aliphatic hydrocarbons, e.g. Chlorobenzene, chloroethylene, or methylene chloride, aliphatic hydrocarbons, e.g. Cyclohexane, paraffins, petroleum fractions, mineral and vegetable oils, alcohols such as e.g. Methanol, ethanol, iso-propanol, butanol or glycol and their ethers and esters, ketones such as e.g. Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents such as dimethyl sulfoxide and water.

Grundsätzlich können alle geeigneten Trägerstoffe eingesetzt werden. Als Trägerstoffe kommen insbesondere infrage: z.B. Ammoniumsalze und natürliche Gesteinsmehle wie Kaoline, Tonerden, Talkum, Kreide, Quarz, Attapulgit, Montmorillonit oder Diatomeenerde und synthetische Gesteinsmehl, wie hochdisperse Kieselsäure, Aluminiumoxid und natürliche oder synthetische Silikate, Harze, Wachse und /oder feste Düngemittel. Mischungen solcher Trägerstoffe können ebenfalls verwendet werden. Als Trägerstoffe für Granulate kommen infrage: z.B. gebrochene und fraktionierte natürliche Gesteine wie Calcit, Marmor, Bims, Sepiolith, Dolomit sowie synthetische Granulate aus anorganischen und organischen Mehlen sowie Granulate aus organischem Material wie Sägemehl, Papier, Kokosnussschalen, Maiskolben und Tabakstängel.In principle, all suitable carriers can be used. Suitable carriers are in particular: for example, ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock flour, such as finely divided silica, alumina and natural or synthetic silicates, resins, waxes and / or solid fertilizers. Mixtures of such carriers can also be used. Suitable carriers for granules are: eg broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, paper, coconut shells, corn cobs and tobacco stems.

Auch verflüssigte gasförmige Streckmittel oder Lösemittel können eingesetzt werden. Insbesondere eignen sich solche Streckmittel oder Trägerstoffe, welche bei normaler Temperatur und unter Normaldruck gasförmig sind, z.B. Aerosol-Treibgase wie Halogenkohlenwasserstoffe sowie Butan, Propan, Stickstoff und Kohlendioxid.Also, liquefied gaseous diluents or solvents can be used. Particularly suitable are those diluents or carriers which are gaseous at normal temperature and under normal pressure, e.g. Aerosol propellants such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.

Beispiele für Emulgier- und/oder Schaum erzeugende Mittel, Dispergiermittel oder Benetzungsmittel mit ionischen oder nicht-ionischen Eigenschaften oder Mischungen dieser oberflächenaktiven Stoffe sind Salze von Polyacrylsäure, Salze von Lignosulphonsäure, Salze von Phenolsulphonsäure oder Naphthalinsulphonsäure, Polykondensate von Ethylenoxid mit Fettalkoholen oder mit Fettsäuren oder mit Fettaminen, mit substituierten Phenolen (vorzugsweise Alkylphenole oder Arylphenole), Salze von Sulphobernsteinsäureestern, Taurinderivate (vorzugsweise Alkyltaurate), Phosphorsäureester von polyethoxylierten Alkoholen oder Phenole, Fettsäureester von Polyolen und Derivate der Verbindungen enthaltend Sulphate, Sulphonate und Phosphate, z.B. Alkylarylpolyglycolether, Alkylsulfonate, Alkylsulfate, Arylsulfonate, Eiweißhydrolysate, Lignin-Sulfitablaugen und Methylcellulose. Die Anwesenheit einer oberflächenaktiven Substanz ist vorteilhaft, wenn eine der Verbindungen der Formel (I) und/oder einer der inerten Trägerstoffe nicht in Wasser löslich ist und wenn die Anwendung in Wasser erfolgt.Examples of emulsifying and / or foaming agents, dispersants or wetting agents having ionic or non-ionic properties or mixtures of these surfactants are salts of polyacrylic acid, salts of lignosulphonic acid, salts of phenolsulphonic acid or naphthalenesulphonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, with substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic acid esters, taurine derivatives (preferably alkyl taurates), phosphoric acid esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols and derivatives of the compounds containing sulphates, sulphonates and phosphates, eg Alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates, protein hydrolysates, lignin-sulphite liquors and methylcellulose. The presence of a surfactant is advantageous when one of the compounds of formula (I) and / or one of the inert carriers is not soluble in water and when applied in water.

Als weitere Hilfsstoffe können in den Formulierungen und den daraus abgeleiteten Anwendungsformen Farbstoffe wie anorganische Pigmente, z.B. Eisenoxid, Titanoxid, Ferrocyanblau und organische Farbstoffe wie Alizarin-, Azo- und Metallphthalocyaninfarbstoffe und Nähr- und Spurennährstoffe wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink vorhanden sein.As further adjuvants, in the formulations and the applications derived therefrom, dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and nutrient and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

Weiterhin enthalten sein können Stabilisatoren wie Kältestabilisatoren, Konservierungsmittel, Oxidationsschutzmittel, Lichtschutzmittel oder andere die chemische und / oder physikalische Stabilität verbessernde Mittel. Weiterhin enthalten sein können schaumerzeugende Mittel oder Entschäumer.Stabilizers such as cold stabilizers, preservatives, antioxidants, light stabilizers or other chemical and / or physical stability-improving agents may also be present. It may also contain foam-forming agents or defoamers.

Ferner können die Formulierungen und daraus abgeleiteten Anwendungsformen als zusätzliche Hilfsstoffe auch Haftmittel wie Carboxymethylcellulose, natürliche und synthetische pulverige, körnige oder latexförmige Polymere enthalten wie Gummiarabikum, Polyvinylalkohol, Polyvinylacetat sowie natürliche Phospholipide wie Kephaline und Lecithine und synthetische Phospholipide. Weitere Hilfsstoffe können mineralische und vegetabile Öle sein.In addition, the formulations and the use forms derived therefrom may also contain, as additional auxiliaries, adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-containing polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural phospholipids such as cephalins and lecithins and synthetic phospholipids. Other auxiliaries may be mineral and vegetable oils.

Gegebenenfalls können noch weitere Hilfsstoffe in den Formulierungen und den daraus abgeleiteten Anwendungsformen enthalten sein. Solche Zusatzstoffe sind beispielsweise Duftstoffe, schützende Kolloide, Bindemittel, Klebstoffe, Verdicker, thixotrope Stoffe, Penetrationsförderer, Retentionsförderer, Stabilisatoren, Sequestiermittel, Komplexbildner, Humectans, Spreitmittel. Im Allgemeinen können die Verbindungen der Formel (I) mit jedem festen oder flüssigen Zusatzstoff, welches für Formulierungszwecke gewöhnlich verwendet wird, kombiniert werden.Optionally, further auxiliaries may be present in the formulations and in the use forms derived therefrom. Such additives are, for example, fragrances, protective colloids, binders, adhesives, thickeners, thixotropic substances, penetration promoters, retention promoters, stabilizers, sequestrants, complexing agents, humectants, spreading agents. In general, the compounds of formula (I) may be combined with any solid or liquid additive commonly used for formulation purposes.

Als Retentionsförderer kommen alle diejenigen Substanzen in Betracht, die die dynamische Oberflächenspannung verringern wie beispielsweise Dioctylsulfosuccinat oder die die Visko-Elastizität erhöhen wie beispielsweise Hydroxypropyl-guar Polymere.As retention promoters are all those substances which reduce the dynamic surface tension such as dioctylsulfosuccinate or increase the visco-elasticity such as hydroxypropyl guar polymers.

Als Penetrationsförderer kommen im vorliegenden Zusammenhang alle diejenigen Substanzen in Betracht, die üblicherweise eingesetzt werden, um das Eindringen von agrochemischen Wirkstoffen in Pflanzen zu verbessern. Penetrationsförderer werden in diesem Zusammenhang dadurch definiert, dass sie aus der (in der Regel wässerigen) Applikationsbrühe und/oder aus dem Spritzbelag in die Kutikula der Pflanze eindringen und dadurch die Stoffbeweglichkeit (Mobilität) der Wirkstoffe in der Kutikula erhöhen können. Die in der Literatur ( Baur et al., 1997, Pesticide Science 51, 131-152 ) beschriebene Methode kann zur Bestimmung dieser Eigenschaft eingesetzt werden. Beispielhaft werden genannt Alkoholalkoxylate wie beispielsweise Kokosfettethoxylat (10) oder Isotridecylethoxylat (12), Fettsäureester wie beispielsweise Rapsöl- oder Sojaölmethylester, Fettamine Alkoxylate wie beispielsweise Tallowamine-ethoxylat (15) oder Ammonium- und/oder Phosphonium-Salze wie beispielsweise Ammoniumsulfat oder Diammonium-hydrogenphosphat.Suitable penetration promoters in the present context are all those substances which are usually used to improve the penetration of agrochemical active substances into plants. Penetration promoters are in this context defined by the fact that they can penetrate from the (usually aqueous) application broth and / or from the spray coating into the cuticle of the plant and thereby increase the material mobility (mobility) of the active ingredients in the cuticle. The in the literature ( Baur et al., 1997, Pesticide Science 51, 131-152 ) method can be used to determine this property. Examples include alcohol alkoxylates such as coconut oil ethoxylate (10) or isotridecyl ethoxylate (12), fatty acid esters such as rapeseed oil or soybean oil, fatty amine alkoxylates such as tallowamine ethoxylate (15) or ammonium and / or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate ,

Die Formulierungen enthalten bevorzugt zwischen 0,00000001 und 98 Gew.-% der Verbindung der Formel (I), besonders bevorzugt zwischen 0,01 und 95 Gew.-% der Verbindung der Formel (I), ganz besonders bevorzugt zwischen 0,5 und 90 Gew.-% der Verbindung der Formel (I), bezogen auf das Gewicht der Formulierung.The formulations preferably contain between 0.00000001 and 98 wt .-% of the compound of formula (I), more preferably between 0.01 and 95 wt .-% of the compound of formula (I), most preferably between 0.5 and 90% by weight of the compound of formula (I), based on the weight of the formulation.

Der Gehalt an der Verbindung der Formel (I) in den aus den Formulierungen bereiteten Anwendungsformen (insbesondere Schädlingsbekämpfungsmittel) kann in weiten Bereichen variieren. Die Konzentration der Verbindung der Formel (I) in den Anwendungsformen kann üblicherweise zwischen 0,00000001 und 95 Gew.-% der Verbindung der Formel (I), vorzugsweise zwischen 0,00001 und 1 Gew.-%, bezogen auf das Gewicht der Anwendungsform, liegen. Die Anwendung geschieht in einer den Anwendungsformen angepaßten üblichen Weise.The content of the compound of the formula (I) in the forms of application prepared from the formulations (in particular pesticides) can vary within wide ranges. The concentration of the compound of the formula (I) in the use forms may usually be between 0.00000001 and 95% by weight of the compound of the formula (I), preferably between 0.00001 and 1% by weight, based on the weight of the application form , lie. The application is done in a custom forms adapted to the application.

Mischungenmixtures

Die Verbindungen der Formel (I) können auch in Mischung mit einem oder mehreren geeigneten Fungiziden, Bakteriziden, Akariziden, Molluskiziden, Nematiziden, Insektiziden, Mikrobiologika, Nützlingen, Herbizide, Düngemitteln, Vogelrepellentien, Phytotonics, Sterilantien, Safenern, Semiochemicals und/oder Pflanzenwachstumsregulatoren verwendet werden, um so z.B. das Wirkungsspektrum zu verbreitern, die Wirkdauer zu verlängern, die Wirkgeschwindigkeit zu steigern, Repellenz zu verhindern oder Resistenzentwicklungen vorzubeugen. Desweiteren können solche Wirkstoffkombinationen das Pflanzenwachstum und/oder die Toleranz gegenüber abiotischen Faktoren wie z. B. hohen oder niedrigen Temperaturen, gegen Trockenheit oder gegen erhöhten Wasser- bzw. Bodensalzgehalt verbessern. Auch lässt sich das Blüh- und Fruchtverhalten verbessern, die Keimfähigkeit und Bewurzelung optimieren, die Ernte erleichtern und Ernteerträge steigern, die Reife beeinflussen, die Qualität und/oder den Ernährungswert der Ernteprodukte steigern, die Lagerfähigkeit verlängern und/oder die Bearbeitbarkeit der Ernteprodukte verbessern.The compounds of formula (I) may also be used in admixture with one or more suitable fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficials, herbicides, fertilizers, avian repellents, phytotonics, sterilants, safeners, Semiochemicals and / or plant growth regulators can be used, for example, to broaden the spectrum of action, to extend the duration of action, to increase the rate of action, to prevent repellence or to prevent development of resistance. Furthermore, such drug combinations plant growth and / or tolerance to abiotic factors such. As high or low temperatures, improve against dryness or increased water or Bodensalzgehalt. Also, flowering and fruiting behavior can be improved, germination and rooting can be improved, harvesting and crop yields increased, maturity can be enhanced, crop quality and / or nutritional value increased, shelf life extended and / or crop productivity improved.

Weiterhin können die Verbindungen der Formel (I) in Mischung mit weiteren Wirkstoffen oder Semiochemicals, wie Lockstoffen und/oder Vogelrepellentien und/oder Pflanzenaktivatoren und/oder Wachstumsregulatoren und/oder Düngemitteln vorliegen. Gleichfalls können die Verbindungen der Formel (I) in Mischungen mit Mitteln zur Verbesserung der Pflanzeneigenschaften wie zum Beispiel Wuchs, Ertrag und Qualität des Erntegutes eingesetzt werden.Furthermore, the compounds of the formula (I) may be present in admixture with other active substances or semiochemicals such as attractants and / or avian repellents and / or plant activators and / or growth regulators and / or fertilizers. Likewise, the compounds of the formula (I) can be used in mixtures with agents for improving plant properties such as, for example, growth, yield and quality of the crop.

In einer besonderen erfindungsgemäßen Ausführungsform liegen die Verbindungen der Formel (I) in Formulierungen bzw. in den aus diesen Formulierungen bereiteten Anwendungsformen in Mischung mit weiteren Verbindungen vor, vorzugsweise solchen wie nachstehend beschrieben.In a particular embodiment of the invention, the compounds of the formula (I) are present in formulations or in the formulations prepared from these formulations in admixture with other compounds, preferably those as described below.

Wenn eine der im Folgenden genannten Verbindungen in verschiedenen tautomeren Formen vorkommen kann sind auch diese Formen mit umfasst, auch wenn sie sie nicht in jedem Fall explizit genannt wurden.If one of the following compounds can occur in different tautomeric forms, these forms are also included, even if they were not explicitly mentioned in each case.

Insektizide / Akarizide / NematizideInsecticides / acaricides / nematicides

Die hier mit ihrem "common name" genannten Wirkstoffe sind bekannt und beispielsweise im Pestizidhandbuch (" The Pesticide Manual" 16th Ed., British Crop Protection Council 2012 ) beschrieben oder im Internet recherchierbar (z.B. http://www.alanwood.net/pesticides).

  • (1) Acetylcholinesterase (AChE) Inhibitoren, wie beispielsweise Carbamate, z.B. Alanycarb, Aldicarb, Bendiocarb, Benfuracarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Ethiofencarb, Fenobucarb, Formetanate, Furathiocarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Propoxur, Thiodicarb, Thiofanox, Triazamate, Trimethacarb, XMC und Xylylcarb oder organophosphate, z.B. Acephate, Azamethiphos, Azinphos-ethyl, Azinphos-methyl, Cadusafos, Chlorethoxyfos, Chlorfenvinphos, Chlormephos, Chlorpyrifos, Chlorpyrifos-methyl, Coumaphos, Cyanophos, Demeton-S-methyl, Diazinon, Dichlorvos/DDVP, Dicrotophos, Dimethoate, Dimethylvinphos, Disulfoton, EPN, Ethion, Ethoprophos, Famphur, Fenamiphos, Fenitrothion, Fenthion, Fosthiazate, Heptenophos, Imicyafos, Isofenphos, Isopropyl O-(methoxyaminothio-phosphoryl) salicylat, Isoxathion, Malathion, Mecarbam, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion, Parathion-methyl, Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimiphos-methyl, Profenofos, Propetamphos, Prothiofos, Pyraclofos, Pyridaphenthion, Quinalphos, Sulfotep, Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos, Triclorfon und Vamidothion.
  • (2) GABA-gesteuerte Chlorid-Kanal-Antagonisten, wie beispielsweise Cyclodien-organochlorine, z.B. Chlordane und Endosulfan oder Phenylpyrazole (Fiprole), z.B. Ethiprole und Fipronil.
  • (3) Natrium-Kanal-Modulatoren / Spannungsabhängige Natrium-Kanal-Blocker, wie beispielsweise Pyrethroide, z.B. Acrinathrin, Allethrin, d-cis-trans Allethrin, d-trans Allethrin, Bifenthrin, Bioallethrin, Bioallethrin S-cyclopentenyl Isomer, Bioresmethrin, Cycloprothrin, Cyfluthrin, beta-Cyfluthrin, Cyhalothrin, lambda-Cyhalothrin, gamma-Cyhalothrin, Cypermethrin, alpha-Cypermethrin, beta-Cypermethrin, theta-Cypermethrin, zeta-Cypermethrin, Cyphenothrin [(1R)-trans-Isomere], Deltamethrin, Empenthrin [(EZ)-(1R)-Isomere), Esfenvalerate, Etofenprox, Fenpropathrin, Fenvalerate, Flucythrinate, Flumethrin, tau-Fluvalinate, Halfenprox, Imiprothrin, Kadethrin, Permethrin, Phenothrin [(1R)-trans-Isomer), Prallethrin, Pyrethrine (pyrethrum), Resmethrin, Silafluofen, Tefluthrin, Tetramethrin, Tetramethrin [(1R)-Isomere)], Tralomethrin und Transfluthrin oder DDT oder Methoxychlor.
  • (4) Nikotinerge Acetylcholin-Rezeptor (nAChR) Agonisten, wie beispielsweise Neonikotinoide, z.B. Acetamiprid, Clothianidin, Dinotefuran, Imidacloprid, Nitenpyram, Thiacloprid und Thiamethoxam oder Nikotin oder Sulfoxaflor oder Flupyradifurone.
  • (5) Nikotinerge Acetylcholin-Rezeptor (nAChR) allosterische Aktivatoren, wie beispielsweise Spinosine, z.B. Spinetoram und Spinosad.
  • (6) Chlorid-Kanal-Aktivatoren, wie beispielsweise Avermectine/Milbemycine, z.B. Abamectin, Emamectin-benzoat, Lepimectin und Milbemectin.
  • (7) Juvenilhormon-Imitatoren, wie beispielsweise Juvenilhormon-Analoge, z.B. Hydroprene, Kinoprene und Methoprene oder Fenoxycarb oder Pyriproxyfen.
  • (8) Wirkstoffe mit unbekannten oder nicht spezifischen Wirkmechanismen, wie beispielsweise Alkylhalide, z.B. Methylbromid und andere Alkylhalide; oderChloropicrin oder Sulfurylfluorid oder Borax oder Brechweinstein.
  • (9) Selektive Fraßhemmer, z.B. Pymetrozine oder Flonicamid.
  • (10) Milbenwachstumsinhibitoren, z.B. Clofentezine, Hexythiazox und Diflovidazin oder Etoxazole.
  • (11) Mikrobielle Disruptoren der Insektendarmmembran, z.B. Bacillus thuringiensis Subspezies israelensis, Bacillus sphaericus, Bacillus thuringiensis Subspezies aizawai, Bacillus thuringiensis Subspezies kurstaki, Bacillus thuringiensis Subspezies tenebrionis und BT Pflanzenproteine: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34/35Ab1.
  • (12) Inhibitoren der oxidativen Phosphorylierung, ATP-Disruptoren, wie beispielsweise Diafenthiuron oder Organozinnverbindungen, z.B. Azocyclotin, Cyhexatin und Fenbutatin-oxid oder Propargite oder Tetradifon.
  • (13) Entkoppler der oxidativen Phoshorylierung durch Unterbrechung des H-Protongradienten, wie beispielsweise Chlorfenapyr, DNOC und Sulfluramid.
  • (14) Nikotinerge Acetylcholin-Rezeptor-Antagonisten, wie beispielsweise Bensultap, Cartaphydrochlorid, Thiocyclam und Thiosultap-Natrium.
  • (15) Inhibitoren der Chitinbiosynthese, Typ 0, wie beispielsweise Bistrifluron, Chlorfluazuron, Diflubenzuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Noviflumuron, Teflubenzuron und Triflumuron.
  • (16) Inhibitoren der Chitinbiosynthese, Typ 1, wie beispielsweise Buprofezin.
  • (17) Häutungshemmer (insbesondere bei Dipteren, d.h.Zweiflüglern), wie beispielsweise Cyromazine.
  • (18) Ecdyson-Rezeptor Agonisten, wie beispielsweise Chromafenozide, Halofenozide, Methoxyfenozide und Tebufenozide.
  • (19) Oktopaminerge Agonisten, wie beispielsweise Amitraz.
  • (20) Komplex-III-Elektronentransportinhibitoren, wie beispielsweise Hydramethylnon oder Acequinocyl oder Fluacrypyrim.
  • (21) Komplex-I-Elektronentransportinhibitoren, beispielsweise METI-Akarizide, z.B. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad und Tolfenpyrad oder Rotenone (Derris).
  • (22) Spannungsabhängige Natriumkanal-Blocker, z.B. Indoxacarb oder Metaflumizone.
  • (23) Inhibitoren der Acetyl-CoA-Carboxylase, wie beispielsweise Tetron- und Tetramsäurederivate, z.B. Spirodiclofen, Spiromesifen und Spirotetramat.
  • (24) Komplex-IV-Elektronentransportinhibitoren, wie beispielsweise Phosphine, z.B. Aluminiumphosphid, Calciumphosphid, Phosphin und Zinkphosphid oder Cyanid.
  • (25) Komplex-II-Elektronentransportinhibitoren, wie beispielsweise Cyenopyrafen und Cyflumetofen.
  • (28) Ryanodinrezeptor-Effektoren, wie beispielsweise Diamide, z.B. Chlorantraniliprole, Cyantraniliprole und Flubendiamide.
The active substances mentioned here with their "common name" are known and, for example, in the pesticide handbook (" The Pesticide Manual "16th ed., British Crop Protection Council 2012 ) or searchable on the Internet (eg http://www.alanwood.net/pesticides).
  • (1) acetylcholinesterase (AChE) inhibitors such as carbamates, eg alanycarb, aldicarb, bendocarb, benfuracarb, butocarboxime, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, Pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb or organophosphates, eg acephates, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chloroethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton -S-methyl, diazinon, dichlorvos / DDVP, dicrotophos, dimethoates, dimethylvinphos, disulfonone, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthione, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O- (methoxyaminothio-phosphoryl) salicylate , Isoxathione, Malathion, Mecarbam, Methamidophos, Methidathione, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion, Parathion-methyl, Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimiphos-methyl, Profenofos, Propetamphos, Prothiofos, Pyraclofos, Pyridaphenthion, Quinalphos, Sulfotep, Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos, Triclorfon and Vamidothion.
  • (2) GABA-controlled chloride channel antagonists, such as cyclodiene organochlorines, eg, chlordanes and endosulfan or phenylpyrazoles (fiproles), eg, ethiprole and fipronil.
  • (3) Sodium channel modulators / voltage dependent sodium channel blockers such as pyrethroids such as acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl isomer, bioresmethrin, cycloprothrin , Cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(1R) -trans isomers], deltamethrin, empenthrin [ (EZ) - (1R) -isomers), esfenvalerates, etofenprox, fenpropathrin, fenvalerates, flucythrinates, flumethrin, tau-fluvalinates, halfenprox, imiprothrin, kadethrin, permethrin, phenothrin [(1R) -trans-isomer), prallethrin, pyrethrins ( pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R) isomers)], tralomethrin and transfluthrin, or DDT or methoxychlor.
  • (4) nicotinergic acetylcholine receptor (nAChR) agonists, such as neonicotinoids, eg acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupyradifurone.
  • (5) nicotinergic acetylcholine receptor (nAChR) allosteric activators such as spinosines, eg spinetoram and spinosad.
  • (6) Chloride channel activators, such as avermectins / milbemycins, eg, abamectin, emamectin benzoate, lepimectin, and milbemectin.
  • (7) Juvenile hormone imitators, such as juvenile hormone analogs, eg, hydroprene, kinoprenes and methoprenes, or fenoxycarb or pyriproxyfen.
  • (8) agents with unknown or nonspecific modes of action, such as alkyl halides, eg, methyl bromide and other alkyl halides; or chloropicrin or sulfuryl fluoride or borax or tartar emetic.
  • (9) Selective feed inhibitors, eg pymetrozine or flonicamide.
  • (10) mite growth inhibitors, eg clofentezine, hexythiazox and diflovidazine or etoxazole.
  • (11) Microbial disruptors of the insect gut membrane, eg Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis and BT plant proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35Ab1.
  • (12) inhibitors of oxidative phosphorylation, ATP disruptors, such as, for example, diafenthiuron or organotin compounds, eg azocyclotine, cyhexatin and fenbutatin oxide or propargite or tetradifone.
  • (13) Decoupling of oxidative phosphorylation by interruption of the H proton gradient, such as chlorfenapyr, DNOC, and sulfluramide.
  • (14) Nicotinergic acetylcholine receptor antagonists such as Bensultap, Cartaprochloride, Thiocyclam and Thiosultap Sodium.
  • (15) Type 0 inhibitors of chitin biosynthesis, such as bistrifluron, chlorofluorazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.
  • (16) inhibitors of chitin biosynthesis, type 1, such as buprofezin.
  • (17) Moulting inhibitors (especially in dipterans, ie tails), such as Cyromazine.
  • (18) ecdysone receptor agonists, such as chromafenozides, halofenozides, methoxyfenozides, and tebufenozides.
  • (19) Octopaminergic agonists, such as amitraz.
  • (20) Complex III electron transport inhibitors such as, for example, hydramethylnone or acequinocyl or fluacrypyrim.
  • (21) complex I electron transport inhibitors, for example METI acaricides, eg fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad or rotenone (Derris).
  • (22) Voltage-dependent sodium channel blockers, eg indoxacarb or metaflumizone.
  • (23) inhibitors of acetyl-CoA carboxylase, such as tetronic and tetramic acid derivatives, eg spirodiclofen, spiromesifen and spirotetramat.
  • (24) complex IV electron transport inhibitors such as phosphines, eg, aluminum phosphide, calcium phosphide, phosphine, and zinc phosphide or cyanide.
  • (25) Complex II electron transport inhibitors such as cyenopyrafen and cyflumetofen.
  • (28) Ryanodine receptor effectors, such as diamides, for example chlorantraniliprole, cyantraniliprole and flubendiamide.

Weitere Wirkstoffe mit unbekanntem oder nicht eindeutigem Wirkmechanismus, wie beispielsweise Afidopyropen, Afoxolaner, Azadirachtin, Benclothiaz, Benzoximate, Bifenazate, Bromopropylate, Chinomethionat, Cryolite, Cyclaniliprole, Cycloxaprid, Cyhalodiamide Dicloromezotiaz, Dicofol, Diflovidazin, Flometoquin, Fluensulfone, Flufenerim, Flufenoxystrobin, Flufiprole, Fluhexafon, Fluopyram, Fluralaner, Fufenozide, Guadipyr, Heptafluthrin, Imidaclothiz, Iprodione, Meperfluthrin, Paichongding, Pyflubumide, Pyridalyl, Pyrifluquinazon, Pyriminostrobin, Tetramethylfluthrin, Tetraniliprole, Tetrachlorantraniliprole, Tioxazafen, Triflumezopyrim und Iodmethan; desweiteren Präparate auf Basis von Bacillus firmus (I-1582, BioNeem, Votivo), sowie folgende bekannte wirksame Verbindungen: 1-{2-Fluor-4-methyl-5-[(2,2,2-trifluorethyl)sulfinyl]phenyl}-3-(trifluormethyl)-1H-1,2,4-triazol-5-amin (bekannt aus WO2006/043635 ), {1'-[(2E)-3-(4-Chlorphenyl)prop-2-en-1-yl]-5-fluorspiro[indol-3,4'-piperidin]-1(2H)-yl}(2-chlorpyridin-4-yl)methanon (bekannt aus WO2003/106457 ), 2-Chlor-N-[2-{1-[(2E)-3-(4-chlorphenyl)prop-2-en-1-yl]piperidin-4-yl}-4-(trifluormethyl)phenyl]isonicotinamid (bekannt aus WO2006/003494 ), 3-(2,5-Dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-on (bekannt aus WO2009/049851 ), 3-(2,5-Dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-yl-ethylcarbonat (bekannt aus WO2009/049851 ), 4-(But-2-in-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluorpyrimidin (bekannt aus WO2004/099160 ), 4-(But-2-in-1-yloxy)-6-(3-chlorphenyl)pyrimidin (bekannt aus WO2003/076415 ), PF1364 ( CAS-Reg.No. 1204776-60-2 ), Methyl-2-[2-({[3-brom-1-(3-chlorpyridin-2-yl)-1H-pyrazol-5-yl]carbonyl} amino)-5-chlor-3-methylbenzoyl]-2-methylhydrazincarboxylat (bekannt aus WO2005/085216 ), Methyl-2-[2-({[3-brom-1-(3-chlorpyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-cyan-3-methylbenzoyl]-2-ethylhydrazincarboxylat (bekannt aus WO2005/085216 ), Methyl-2-[2-({[3-brom-1-(3-chlorpyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-cyan-3-methylbenzoyl]-2-methylhydrazincarboxylat (bekannt aus WO2005/085216 ), Methyl-2-[3,5-dibrom-2-({[3-brom-1-(3-chlorpyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl]-2-ethylhydrazincarboxylat (bekannt aus WO2005/085216 ), N-[2-(5-Amino-1,3,4-thiadiazol-2-yl)-4-chlor-6-methylphenyl]-3-brom-1-(3-chlorpyridin-2-yl)-1H-pyrazol-5-carboxamid (bekannt aus CN102057925 ), 8-Chlor-N-[(2-chlor-5-methoxyphenyl)sulfonyl]-6-(trifluormethyl)imidazo[1,2-a]pyridin-2-carboxamid (bekannt aus WO2010/129500 ), 4-[5-(3,5-Dichlorphenyl)-5-(trifluormethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxidothietan-3-yl)benzamid (bekannt aus WO2009/080250 ), N-[(2E)-1-[(6-Chlorpyridin-3-yl)methyl]pyridin-2(1H)-yliden]-2,2,2-trifluoracetamid (bekannt aus WO2012/029672 ), 1-[(2-Chlor-1,3-thiazol-5-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olat (bekannt aus WO2009/099929 ), 1-[(6-Chlorpyridin-3-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olat (bekannt aus WO2009/099929 ), 4-(3-{2,6-Dichlor-4-[(3,3-dichlorprop-2-en-1-yl)oxy]phenoxy}propoxy)-2-methoxy-6-(trifluormethyl)pyrimidin (bekannt aus CN101337940 ), N-[2-(tert-Butylcarbamoyl)-4-chlor-6-methylphenyl]-1-(3-chlorpyridin-2-yl)-3-(fluormethoxy)-1H-pyrazol-5-carboxamid (bekannt aus WO2008/134969 , 3-[Benzoyl(methyl)amino]-N-[2-brom-4-[1,2,2,2-tetrafluor-1-(trifluormethyl)ethyl]-6-(trifluormethyl)phenyl]-2-fluor-benzamid (bekannt aus WO 2010018714 ), Butyl-[2-(2,4-dichlorphenyl)-3-oxo-4-oxaspiro[4.5]dec-1-en-1-yl]-carbonat (bekannt aus CN 102060818 ), 4-[5-(3,5-Dichlorphenyl)-5-(trifluormethyl)-4H-isoxazol-3-yl]-N-[(Z)-methoxyiminomethyl]-2-methyl-benzamid (bekannt aus WO2007/026965 ), 3E)-3-[1-[(6-Chlor-3-pyridyl)methyl]-2-pyridyliden]-1,1,1-trifluor-propan-2-on (bekannt aus WO2013/144213 , N-(Methylsulfonyl)-6-[2-(pyridin-3-yl)-1,3-thiazol-5-yl]pyridin-2-carboxamid (bekannt aus WO2012/000896 ), N-[3-(Benzylcarbamoyl)-4-chlorphenyl]-1-methyl-3-(pentafluorethyl)-4-(trifluormethyl)-1H-pyrazol-5-carboxamid bekannt aus WO2010/051926 ).Other drugs with unknown or ambiguous mechanism of action, such as afidopyropene, afoxolaner, azadirachtin, benclothiaz, benzoximate, bifenazate, bromopropylate, quinomethionate, cryolites, cyclaniliprole, cycloxapride, cyhalodiamide dicloromezotiaz, dicofol, diflovidazine, flometoquine, fluensulfone, flufenerim, flufenoxystrobin, flufiprole, Flaxxafon, Fluopyram, Fluralaner, Fufenozide, Guadipyr, Heptafluthrin, Imidaclothiz, Iprodione, Meperfluthrin, Paichongding, Pyflubumide, Pyralidyl, Pyrifluquinazone, Pyriminostrobin, Tetramethylfluthrin, Tetraniliprole, Tetrachlorantraniliprole, Tioxazafen, Triflumezopyrim and Iodomethane; furthermore preparations based on Bacillus firmus (I-1582, BioNeem, Votivo), and the following known active compounds: 1- {2-fluoro-4-methyl-5 - [(2,2,2-trifluoroethyl) sulfinyl] phenyl} -3- (trifluoromethyl) -1H-1,2,4-triazole-5-amine (known from WO2006 / 043635 ), {1 '- [(2E) -3- (4-chlorophenyl) prop-2-en-1-yl] -5-fluorospiro [indole-3,4'-piperidine] -1 (2H) -yl} (2-chloropyridin-4-yl) methanone (known from WO2003 / 106457 ), 2-chloro-N- [2- {1 - [(2E) -3- (4-chlorophenyl) -prop-2-en-1-yl] -piperidin-4-yl} -4- (trifluoromethyl) -phenyl] isonicotinamide (known from WO2006 / 003494 ), 3- (2,5-dimethylphenyl) -4-hydroxy-8-methoxy-1,8-diazaspiro [4.5] dec-3-en-2-one (known from WO2009 / 049851 ), 3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-1,8-diazaspiro [4.5] dec-3-en-4-yl-ethyl carbonate (known from WO2009 / 049851 ), 4- (But-2-yn-1-yloxy) -6- (3,5-dimethylpiperidin-1-yl) -5-fluoropyrimidine (known from WO2004 / 099160 ), 4- (But-2-yn-1-yloxy) -6- (3-chlorophenyl) pyrimidine (Known from WO2003 / 076415 ), PF1364 ( CAS-Reg.No. 1204776-60-2 ), Methyl 2- [2 - ({[3-bromo-1- (3-chloropyridin-2-yl) -1H-pyrazol-5-yl] carbonyl} amino) -5-chloro-3-methylbenzoyl] - 2-methylhydrazinecarboxylate (known from WO2005 / 085216 ), Methyl 2- [2 - ({[3-bromo-1- (3-chloropyridin-2-yl) -1H-pyrazol-5-yl] carbonyl} amino) -5-cyano-3-methylbenzoyl] - 2-ethylhydrazinecarboxylate (known from WO2005 / 085216 ), Methyl 2- [2 - ({[3-bromo-1- (3-chloropyridin-2-yl) -1H-pyrazol-5-yl] carbonyl} amino) -5-cyano-3-methylbenzoyl] - 2-methylhydrazinecarboxylate (known from WO2005 / 085216 ), Methyl 2- [3,5-dibromo-2 - ({[3-bromo-1- (3-chloropyridin-2-yl) -1H-pyrazol-5-yl] carbonyl} amino) benzoyl] -2 Ethylhydrazinecarboxylate (known from WO2005 / 085216 ), N- [2- (5-amino-1,3,4-thiadiazol-2-yl) -4-chloro-6-methylphenyl] -3-bromo-1- (3-chloropyridin-2-yl) - 1H-pyrazole-5-carboxamide (known from CN102057925 ), 8-chloro-N - [(2-chloro-5-methoxyphenyl) sulfonyl] -6- (trifluoromethyl) imidazo [1,2-a] pyridine-2-carboxamide (known from WO2010 / 129500 ), 4- [5- (3,5-dichlorophenyl) -5- (trifluoromethyl) -4,5-dihydro-1,2-oxazol-3-yl] -2-methyl-N- (1-oxidothietane-3 -yl) benzamide (known from WO2009 / 080250 ), N - [(2E) -1 - [(6-chloropyridin-3-yl) methyl] pyridine-2 (1H) -ylidene] -2,2,2-trifluoroacetamide (known from WO2012 / 029672 ), 1 - [(2-chloro-1,3-thiazol-5-yl) methyl] -4-oxo-3-phenyl-4H-pyrido [1,2-a] pyrimidin-1-ium-2-olate (known from WO2009 / 099929 ), 1 - [(6-chloropyridin-3-yl) methyl] -4-oxo-3-phenyl-4H-pyrido [1,2-a] pyrimidin-1-ium-2-olate (known from WO2009 / 099929 ), 4- (3- {2,6-dichloro-4 - [(3,3-dichloroprop-2-en-1-yl) oxy] phenoxy} propoxy) -2-methoxy-6- (trifluoromethyl) pyrimidine ( known from CN101337940 ), N- [2- (tert -butylcarbamoyl) -4-chloro-6-methylphenyl] -1- (3-chloropyridin-2-yl) -3- (fluoromethoxy) -1H-pyrazole-5-carboxamide (known from WO2008 / 134969 , 3- [Benzoyl (methyl) amino] -N- [2-bromo-4- [1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethyl] -6- (trifluoromethyl) phenyl] -2-fluoro benzamide (known from WO 2010018714 ), Butyl [2- (2,4-dichlorophenyl) -3-oxo-4-oxaspiro [4.5] dec-1-en-1-yl] carbonate (known from CN 102060818 ), 4- [5- (3,5-dichlorophenyl) -5- (trifluoromethyl) -4H-isoxazol-3-yl] -N - [(Z) -methoxyiminomethyl] -2-methylbenzamide (known from WO2007 / 026965 ), 3E) -3- [1 - [(6-chloro-3-pyridyl) methyl] -2-pyridylidene] -1,1,1-trifluoro-propan-2-one (known from WO2013 / 144213 , N- (methylsulfonyl) -6- [2- (pyridin-3-yl) -1,3-thiazol-5-yl] pyridine-2-carboxamide (known from WO2012 / 000896 ), N- [3- (benzylcarbamoyl) -4-chlorophenyl] -1-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazole-5-carboxamide WO2010 / 051926 ).

Fungizidefungicides

Die hier mit ihrem "common name" spezifizierten Wirkstoffe sind bekannt, beispielsweise beschrieben im "Pesticide Manual" oder im Internet (beispielsweise: http://www.alanwood.net/pesticides).The active ingredients specified here with their "common name" are known, for example, described in the "Pesticide Manual" or on the Internet (for example: http://www.alanwood.net/pesticides).

Alle aufgeführten fungiziden Mischpartner der Klassen (1) bis (15) können optional Salze mit entsprechenden Basen oder Säuren bilden, sofern geeignete funktionelle Gruppen vorliegen. Außerdem sind für die aufgeführten fungiziden Mischpartner der Klassen (1) bis (15) auch tautomere Formen eingeschlossen, sofern Tautomerie möglich ist.

  1. 1) Inhibitoren der Ergosterolbiosynthese, zum Beispiel (1.01) Aldimorph, (1.02) Azaconazol, (1.03) Bitertanol, (1.04) Bromuconazol, (1.05) Cyproconazol, (1.06) Diclobutrazol, (1.07) Difenoconazol, (1.08) Diniconazol, (1.09) Diniconazol-M, (1.10) Dodemorph, (1.11) Dodemorphacetat, (1.12) Epoxiconazol, (1.13) Etaconazol, (1.14) Fenarimol, (1.15) Fenbuconazol, (1.16) Fenhexamid, (1.17) Fenpropidin, (1.18) Fenpropimorph, (1.19) Fluquinconazol, (1.20) Flurprimidol, (1.21) Flusilazol, (1.22) Flutriafol, (1.23) Furconazol, (1.24) Furconazol-cis, (1.25) Hexaconazol, (1.26) Imazalil, (1.27) Imazalilsulfat, (1.28) Imibenconazol, (1.29) Ipconazol, (1.30) Metconazol, (1.31) Myclobutanil, (1.32) Naftifin, (1.33) Nuarimol, (1.34) Oxpoconazol, (1.35) Paclobutrazol, (1.36) Pefurazoat, (1.37) Penconazol, (1.38) Piperalin, (1.39) Prochloraz, (1.40) Propiconazol, (1.41) Prothioconazol, (1.42) Pyributicarb, (1.43) Pyrifenox, (1.44) Quinconazol, (1.45) Simeconazol, (1.46) Spiroxamin, (1.47) Tebuconazol, (1.48) Terbinafin, (1.49) Tetraconazol, (1.50) Triadimefon, (1.51) Triadimenol, (1.52) Tridemorph, (1.53) Triflumizol, (1.54) Triforin, (1.55) Triticonazol, (1.56) Uniconazol, (1.57) Uniconazol-p, (1.58) Viniconazol, (1.59) Voriconazol, (1.60) 1-(4-Chlorphenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol, (1.61) 1-(2,2-Dimethyl-2,3-dihydro-1H-inden-1-yl)-1H-imidazol-5-carbonsäuremethylester, (1.62) N'-{5-(Difluormethyl)-2-methyl-4-[3-(trimethylsilyl)propoxy]phenyl}-N-ethyl-N-methylimidoformamid, (1.63) N-Ethyl-N-methyl-N'- {2-methyl-5-(trifluormethyl)-4-[3-(trimethylsilyl)propoxy]phenyl}imidoformamid, (1.64) O-[1-(4-Methoxyphenoxy)-3,3-dimethylbutan-2-yl]-1H-imidazol-1-carbothioat, (1.65) Pyrisoxazol, (1.66) 2-{[3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.67) 1-{[3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanat, (1.68) 5-(Allylsulfanyl)-1-{[3-(2-chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol, (1.69) 2-[1-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.70) 2-{[rel(2R,3S)-3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.71) 2-{[rel(2R,3R)-3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)-oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.72) 1-{[rel(2R,3S)-3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanat, (1.73) 1-{[rel(2R,3R)-3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanat, (1.74) 5-(Allylsulfanyl)-1-{[rel(2R,3S)-3-(2-chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol, (1.75) 5-(Allylsulfanyl)-1-{[rel(2R,3R)-3-(2-chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol, (1.76) 2-[(2S,4S,5S)-1-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.77) 2-[(2R,4S,5S)-1-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.78) 2-[(2R,4R,5R)-1-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.79) 2-[(2S,4R,5R)-1-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.80) 2-[(2S,4S,5R)-1-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.81) 2-[(2R,4S,5R)-1-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.82) 2-[(2R,4R,5S)-1-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.83) 2-[(2S,4R,5S)-1-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.84) 2-[4-(4-Chlorphenoxy)-2-(trifluormethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.85) 2-[4-(4-Chlorphenoxy)-2-(trifluormethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.86) 2-[4-(4-Chlorphenoxy)-2-(trifluormethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)pentan-2-ol, (1.87) 2-[2-Chlor-4-(4-chlorphenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.88) 2-[2-Chlor-4-(2,4-dichlorphenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.89) (2R)-2-(1-Chlorcyclopropyl)-4-[(1R)-2,2-dichlorcyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.90) (2R)-2-(1-Chlorcyclopropyl)-4-[(1S)-2,2-dichlorcyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.91) (2S)-2-(1-Chlorcyclopropyl)-4-[(1S)-2,2-dichlorcyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.92) (2S)-2-(1-Chlorcyclopropyl)-4-[(1R)-2,2-dichlorcyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.93) (1S,2R,5R)-5-(4-Chlorbenzyl)-2-(chlormethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.94)(1R,2S,5S)-5-(4-Chlorbenzyl)-2-(chlormethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.95) 5-(4-Chlorbenzyl)-2-(chlormethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol.
  2. 2) Inhibitoren der Atmungskette am Komplex I oder II, zum Beispiel (2.01) Bixafen, (2.02) Boscalid, (2.03) Carboxin, (2.04) Diflumetorim, (2.05) Fenfuram, (2.06) Fluopyram, (2.07) Flutolanil, (2.08) Fluxapyroxad, (2.09) Furametpyr, (2.10) Furmecyclox, (2.11) Isopyrazam (Mischung von syn-epimerem Racemat 1RS,4SR,9RS und anti-epimerem Racemat 1RS,4SR,9SR), (2.12) Isopyrazam (anti-epimeres Racemat 1RS,4SR,9SR), (2.13) Isopyrazam (anti-epimeres Enantiomer 1R,4S,9S), (2.14) Isopyrazam (anti-epimeres Enantiomer 1S,4R,9R), (2.15) Isopyrazam (syn-epimeres Racemat 1RS,4SR,9RS), (2.16) Isopyrazam (syn-epimeres Enantiomer 1R,4S,9R), (2.17) Isopyrazam (syn-epimeres Enantiomer 1S,4R,9S), (2.18) Mepronil, (2.19) Oxycarboxin, (2.20) Penflufen, (2.21) Penthiopyrad, (2.22) Sedaxan, (2.23) Thifluzamid, (2.24) 1-Methyl-N-[2-(1,1,2,2-tetrafluorethoxy)phenyl]-3-(trifluormethyl)-1H-pyrazol-4-carboxamid, (2.25) 3-(Difluormethyl)-1-methyl-N-[2-(1,1,2,2-tetrafluorethoxy)phenyl]-1H-pyrazol-4-carboxamid, (2.26) 3-(Difluormethyl)-N-[4-fluor-2-(1,1,2,3,3,3-hexafluorpropoxy)phenyl]-1-methyl-1H-pyrazol-4-carboxamid, (2.27) N-[1-(2,4-Dichlorphenyl)-1-methoxypropan-2-yl]-3-(difluormethyl)-1-methyl-1H-pyrazol-4-carboxamid, (2.28) 5,8-Difluor-N-[2-(2-fluor-4-{[4-(trifluormethyl)pyridin-2-yl]oxy}phenyl)ethyl]chinazolin-4-amin, (2.29) Benzovindiflupyr, (2.30) N-[(1S,4R)-9-(Dichlormethylen)-1,2,3,4-tetrahydro-1,4-methanonaphthalin-5-yl]-3-(difluormethyl)-1-methyl-1H-pyrazol-4-carboxamid, (2.31) N-[(1R,4S)-9-(Dichlormethylen)-1,2,3,4-tetrahydro-1,4-methanonaphthalin-5-yl]-3-(difluormethyl)-1-methyl-1H-pyrazol-4-carboxamid, (2.32) 3-(Difluormethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazol-4-carboxamid, (2.33) 1,3,5-Trimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazol-4-carboxamid, (2.34) 1-Methyl-3-(trifluormethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazol-4-carboxamid, (2.35) 1-Methyl-3-(trifluormethyl)-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazol-4-carboxamid, (2.36) 1-Methyl-3-(trifluormethyl)-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazol-4-carboxamid, (2.37) 3-(Difluormethyl)-1-methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazol-4-carboxamid, (2.38) 3-(Difluormethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazol-4-carboxamid, (2.39) 1,3,5-Trimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazol-4-carboxamid, (2.40) 1,3,5-Trimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazol-4-carboxamid, (2.41) Benodanil, (2.42) 2-Chlor-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)pyridin-3-carboxamid, (2.43) Isofetamid, (2.44) 1-Methyl-3-(trifluormethyl)-N-[2'-(trifluormethyl)biphenyl-2-yl]-1H-pyrazol-4-carboxamid, (2.45) N-(4'-Chlorbiphenyl-2-yl)-3-(difluormethyl)-1-methyl-1H-pyrazol-4-carboxamid, (2.46) N-(2',4'-Dichlorbiphenyl-2-yl)-3-(difluormethyl)-1-methyl-1H-pyrazol-4-carboxamid, (2.47) 3-(Difluormethyl)-1-methyl-N-[4'-(trifluormethyl)biphenyl-2-yl]-1H-pyrazol-4-carboxamid, (2.48) N-(2',5'-Difluorbiphenyl-2-yl)-1-methyl-3-(trifluormethyl)-1H-pyrazol-4-carboxamid, (2.49) 3-(Difluormethyl)-1-methyl-N-[4'-(prop-1-in-1-yl)biphenyl-2-yl]-1H-pyrazol-4-carboxamid, (2.50) 5-Fluor-1,3-dimethyl-N-[4'-(prop-1-in-1-yl)biphenyl-2-yl]-1H-pyrazol-4-carboxamid, (2.51) 2-Chlor-N-[4'-(prop-1-in-1-yl)biphenyl-2-yl]nicotinamid, (2.52) 3-(Difluormethyl)-N-[4'-(3,3-dimethylbut-1-in-1-yl)biphenyl-2-yl]-1-methyl-1H-pyrazol-4-carboxamid, (2.53) N-[4'-(3,3-Dimethylbut-1-in-1-yl)biphenyl-2-yl]-5-fluor-1,3-dimethyl-1H-pyrazol-4-carboxamid, (2.54) 3-(Difluormethyl)-N-(4'-ethinylbiphenyl-2-yl)-1-methyl-1H-pyrazol-4-carboxamid, (2.55) N-(4'-Ethinylbiphenyl-2-yl)-5-fluor-1,3-dimethyl-1H-pyrazol-4-carboxamid, (2.56) 2-Chlor-N-(4'-ethinylbiphenyl-2-yl)nicotinamid, (2.57) 2-Chlor-N-[4'-(3,3-dimethylbut-1-in-1-yl)biphenyl-2-yl]nicotinamid, (2.58) 4-(Difluormethyl)-2-methyl-N-[4'-(trifluormethyl)biphenyl-2-yl]-1,3-thiazol-5-carboxamid, (2.59) 5-Fluor-N-[4'-(3-hydroxy-3-methylbut-1-in-1-yl)biphenyl-2-yl]-1,3-dimethyl-1H-pyrazol-4-carboxamid, (2.60) 2-Chlor-N-[4'-(3-hydroxy-3-methylbut-1-in-1-yl)biphenyl-2-yl]nicotinamid, (2.61) 3-(Difluormethyl)-N-[4'-(3-methoxy-3-methylbut-1-in-1-yl)biphenyl-2-yl]-1-methyl-1H-pyrazol-4-carboxamid, (2.62) 5-Fluor-N-[4'-(3-methoxy-3-methylbut-1-in-1-yl)biphenyl-2-yl]-1,3-dimethyl-1H-pyrazol-4-carboxamid, (2.63) 2-Chlor-N-[4'-(3-methoxy-3-methylbut-1-in-1-yl)biphenyl-2-yl]nicotinamid, (2.64) 1,3-Dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazol-4-carboxamid, (2.65) 1,3-Dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazol-4-carboxamid, (2.66) 1,3-Dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazol-4-carboxamid, (2.67) 3-(Difluormethyl)-N-methoxy-1-methyl-N-[1-(2,4,6-trichlorphenyl)propan-2-yl]-1H-pyrazol-4-carboxamid, (2.68) 3-(Difluormethyl)-N-(7-fluor-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1-methyl-1H-pyrazol-4-carboxamid, (2.69) 3-(Difluormethyl)-N-[(3R)-7-fluor-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazol-4-carboxamid, (2.70) 3-(Difluormethyl)-N-[(3S)-7-fluor-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazol-4-carboxamid.
  3. 3) Inhibitoren der Atmungskette am Komplex III, zum Beispiel (3.01) Ametoctradin, (3.02) Amisulbrom, (3.03) Azoxystrobin, (3.04) Cyazofamid, (3.05) Coumethoxystrobin, (3.06) Coumoxystrobin, (3.07) Dimoxystrobin, (3.08) Enoxastrobin, (3.09) Famoxadon, (3.10) Fenamidon, (3.11) Flufenoxystrobin, (3.12) Fluoxastrobin, (3.13) Kresoxim-methyl, (3.14) Metominostrobin, (3.15) Orysastrobin, (3.16) Picoxystrobin, (3.17) Pyraclostrobin, (3.18) Pyrametostrobin, (3.19) Pyraoxystrobin, (3.20) Pyribencarb, (3.21) Triclopyricarb, (3.22) Trifloxystrobin, (3.23) (2E)-2-(2-{[6-(3-Chlor-2-methylphenoxy)-5-fluorpyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N-methyl¬acetamid, (3.24) (2E)-2-(Methoxyimino)-N-methyl-2-(2-{[({(1E)-1-[3-(trifluormethyl)phenyl]¬ethyliden}¬amino)oxy]methyl}phenyl)acetamid, (3.25) (2E)-2-(Methoxyimino)-N-methyl-2-{2-[(E)-({1-[3-(trifluormethyl)phenyl]ethoxy}imino)methyl]phenyl}acetamid, (3.26) (2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-Fluor-2-phenylvinyl]oxy}phenyl)ethyliden]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamid, (3.27) Fenaminostrobin, (3.28) 5-Methoxy-2-methyl-4-(2-{[({(1E)-1-[3-(trifluormethyl)phenyl]ethyliden}amino)oxy]methyl}phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-on, (3.29) (2E)-2-{2-[({Cyclopropyl[(4-methoxyphenyl)imino]methyl} sulfanyl)methyl]phenyl}-3-methoxyacrylsäuremethylester, (3.30) N-(3-Ethyl-3,5,5-trimethylcyclohexyl)-3-formamido-2-hydroxybenzamid, (3.31) 2-{2-[(2,5-Dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamid, (3.32) 2-{2-[(2,5-Dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamid, (3.33) (2E,3Z)-5-{[1-(4-Chlorphenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamid.
  4. 4) Inhibitoren der Mitose und Zellteilung, zum Beispiel (4.01) Benomyl, (4.02) Carbendazim, (4.03) Chlorfenazol, (4.04) Diethofencarb, (4.05) Ethaboxam, (4.06) Fluopicolid, (4.07) Fuberidazol, (4.08) Pencycuron, (4.09) Thiabendazol, (4.10) Thiophanat-methyl, (4.11) Thiophanat, (4.12) Zoxamid, (4.13) 5-Chlor-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorphenyl)[1,2,4]triazolo[1,5-a]pyrimidin, (4.14) 3-Chlor-5-(6-chlorpyridin-3-yl)-6-methyl-4-(2,4,6-trifluorphenyl)pyridazin.
  5. 5) Verbindungen, die dazu fähig sind, an mehreren Stellen anzugreifen ("Multisite Action"), zum Beispiel (5.01) Bordeaux-Mischung, (5.02) Captafol, (5.03) Captan, (5.04) Chlorothalonil, (5.05) Kupferhydroxid, (5.06) Kupfernaphthenat, (5.07) Kupferoxid, (5.08) Kupferoxychlorid, (5.09) Kupfer(2+)-sulfat, (5.10) Dichlofluanid, (5.11) Dithianon, (5.12) Dodin, (5.13) Dodin freie Base, (5.14) Ferbam, (5.15) Fluorofolpet, (5.16) Folpet, (5.17) Guazatin, (5.18) Guazatinacetat, (5.19) Iminoctadin, (5.20) Iminoctadinalbesilat, (5.21) Iminoctadintriacetat, (5.22) Mancopper, (5.23) Mancozeb, (5.24) Maneb, (5.25) Metiram, (5.26) Metiram-Zink, (5.27) Oxin-Kupfer, (5.28) Propamidin, (5.29) Propineb, (5.30) Schwefel und Schwefelzubereitungen einschließlich Calciumpolysulfid, (5.31) Thiram, (5.32) Tolylfluanid, (5.33) Zineb, (5.34) Ziram, (5.35) Anilazin.
  6. 6) Verbindungen, die dazu fähig sind, eine Abwehrreaktion des Wirtes zu induzieren, zum Beispiel (6.01) Acibenzolar-S-methyl, (6.02) Isotianil, (6.03) Probenazol, (6.04) Tiadinil, (6.05) Laminarin.
  7. 7) Inhibitoren der Aminosäure- und/oder Proteinbiosynthese, zum Beispiel (7.01) Andoprim, (7.02) Blasticidin-S, (7.03) Cyprodinil, (7.04) Kasugamycin, (7.05) Kasugamycinhydrochlorid-hydrat, (7.06) Mepanipyrim, (7.07) Pyrimethanil, (7.08) 3-(5-Fluor-3,3,4,4-tetramethyl-3,4-dihydroisochinolin-1-yl)chinolin, (7.09) Oxytetracyclin, (7.10) Streptomycin.
  8. 8) Inhibitoren der ATP-Produktion, zum Beispiel (8.01) Fentinacetat, (8.02) Fentinchlorid, (8.03) Fentinhydroxid, (8.04) Silthiofam.
  9. 9) Inhibitoren der Zellwandsynthese, zum Beispiel (9.01) Benthiavalicarb, (9.02) Dimethomorph, (9.03) Flumorph, (9.04) Iprovalicarb, (9.05) Mandipropamid, (9.06) Polyoxine, (9.07) Polyoxorim, (9.08) Validamycin A, (9.09) Valifenalat, (9.10) Polyoxin B, (9.11) (2E)-3-(4-tert.-Butylphenyl)-3-(2-chlorpyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-on, (9.12) (2Z)-3-(4-tert.-Butylphenyl)-3-(2-chlorpyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-on.
  10. 10) Inhibitoren der Lipid- und Membransynthese, zum Beispiel (10.01) Biphenyl, (10.02) Chloroneb, (10.03) Dicloran, (10.04) Edifenphos, (10.05) Etridiazol, (10.06) Iodocarb, (10.07) Iprobenfos, (10.08) Isoprothiolan, (10.09) Propamocarb, (10.10) Propamocarbhydrochlorid, (10.11) Prothiocarb, (10.12) Pyrazophos, (10.13) Quintozen, (10.14) Tecnazen, (10.15) Tolclofos-methyl.
  11. 11) Inhibitoren der Melaninbiosynthese, zum Beispiel (11.01) Carpropamid, (11.02) Diclocymet, (11.03) Fenoxanil, (11.04) Phthalid, (11.05) Pyroquilon, (11.06) Tricyclazol, (11.07) 2,2,2-Trifluorethyl {3-methyl-1-[(4-methylbenzoyl)amino]butan-2-yl}carbamat.
  12. 12) Inhibitoren der Nukleinsäuresynthese, zum Beispiel (12.01) Benalaxyl, (12.02) Benalaxyl-M (Kiralaxyl), (12.03) Bupirimat, (12.04) Clozylacon, (12.05) Dimethirimol, (12.06) Ethirimol, (12.07) Furalaxyl, (12.08) Hymexazol, (12.09) Metalaxyl, (12.10) Metalaxyl-M (Mefenoxam), (12.11) Ofurace, (12.12) Oxadixyl, (12.13) Oxolinsäure, (12.14) Octhilinon.
  13. 13) Inhibitoren der Signalvermittlung, zum Beispiel (13.01) Chlozolinat, (13.02) Fenpiclonil, (13.03) Fludioxonil, (13.04) Iprodion, (13.05) Procymidon, (13.06) Quinoxyfen, (13.07) Vinclozolin, (13.08) Proquinazid.
  14. 14) Verbindungen, die als Entkoppler wirken können, zum Beispiel (14.01) Binapacryl, (14.02) Dinocap, (14.03) Ferimzon, (14.04) Fluazinam, (14.05) Meptyldinocap.
  15. 15) Weitere Verbindungen, zum Beispiel (15.001) Benthiazol, (15.002) Bethoxazin, (15.003) Capsimycin, (15.004) Carvon, (15.005) Chinomethionat, (15.006) Pyriofenon (Chlazafenon), (15.007) Cufraneb, (15.008) Cyflufenamid, (15.009) Cymoxanil, (15.010) Cyprosulfamid, (15.011) Dazomet, (15.012) Debacarb, (15.013) Dichlorophen, (15.014) Diclomezin, (15.015) Difenzoquat, (15.016) Difenzoquatmetilsulfat, (15.017) Diphenylamin, (15.018) Ecomat, (15.019) Fenpyrazamin, (15.020) Flumetover, (15.021) Fluoroimid, (15.022) Flusulfamid, (15.023) Flutianil, (15.024) Fosetyl-Aluminium, (15.025) Fosetyl-Calcium, (15.026) Fosetyl-Natrium, (15.027) Hexachlorbenzol, (15.028) Irumamycin, (15.029) Methasulfocarb, (15.030) Methylisothiocyanat, (15.031) Metrafenon, (15.032) Mildiomycin, (15.033) Natamycin, (15.034) Nickeldimethyldithiocarbamat, (15.035) Nitrothalisopropyl, (15.036) Oxamocarb, (15.037) Oxyfenthiin, (15.038) Pentachlorphenol und Salze, (15.039) Phenothrin, (15.040) phosphorige Säure und deren Salze, (15.041) Propamocarb-fosetylat, (15.042) Propanosin-Natrium, (15.043) Pyrimorph, (15.044) Pyrrolnitrin, (15.045) Tebufloquin, (15.046) Tecloftalam, (15.047) Tolnifanid, (15.048) Triazoxid, (15.049) Trichlamid, (15.050) Zarilamid, (15.051) 2-Methylpropansäure-(3S,6S,7R,8R)-8-benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-ylester, (15.052) 1-(4-{4-[(5R)-5-(2,6-Difluorphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluormethyl)-1H-pyrazol-1-yl]ethanon, (15.053) 1-(4-{4-[(5S)-5-(2,6-Difluorphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluormethyl)-1H-pyrazol-1-yl]ethanon, (15.054) Oxathiapiprolin, (15.055) 1H-Imidazol-1-carbonsäure-1-(4-methoxyphenoxy)-3,3-dimethylbutan-2-ylester, (15.056) 2,3,5,6-Tetrachlor-4-(methylsulfonyl)pyridin, (15.057) 2,3-Dibutyl-6-chlorthieno[2,3-d]pyrimidin-4(3H)-on, (15.058) 2,6-Dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrol-1,3,5,7(2H,6H)-tetron, (15.059) 2-[5-Methyl-3-(trifluormethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5R)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanon, (15.060) 2-[5-Methyl-3-(trifluormethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5S)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanon, (15.061) 2-[5-Methyl-3-(trifluormethyl)-1H-pyrazol-1-yl]-1-{4-[4-(5-phenyl-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidin-1-yl}ethanon, (15.062) 2-Butoxy-6-iod-3-propyl-4H-chromen-4-on, (15.063) 2-Chlor-5-[2-chlor-1-(2,6-difluor-4-methoxyphenyl)-4-methyl-1H-imidazol-5-yl]pyridin, (15.064) 2-Phenylphenol und Salze, (15.065) 3-(4,4,5-Trifluor-3,3-dimethyl-3,4-dihydroisochinolin-1-yl)chinolin, (15.066) 3,4,5-Trichlorpyridin-2,6-dicarbonsäurenitril, (15.067) 3-Chlor-5-(4-chlorphenyl)-4-(2,6-difluorphenyl)-6-methylpyridazin, (15.068) 4-(4-Chlorphenyl)-5-(2,6-difluorphenyl)-3,6-dimethylpyridazin, (15.069) 5-Amino-1,3,4-thiadiazol-2-thiol, (15.070) 5-Chlor-N'-phenyl-N'-(prop-2-in-1-yl)thiophen-2-sulfonohydrazid, (15.071) 5-Fluor-2-[(4-fluorbenzyl)oxy]pyrimidin-4-amin, (15.072) 5-Fluor-2-[(4-methylbenzyl)oxy]pyrimidin-4-amin, (15.073) 5-Methyl-6-octyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amin, (15.074) (2Z)-3-Amino-2-cyano-3-phenylacrylsäureethylester, (15.075) N'-(4-{[3-(4-Chlorbenzyl)-1,2,4-thiadiazol-5-yl]oxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamid, (15.076) N-(4-Chlorbenzyl)-3-[3-methoxy-4-(prop-2-in-1-yloxy)phenyl]propanamid, (15.077) N-[(4-Chlorphenyl)(cyano)methyl]-3-[3-methoxy-4-(prop-2-in-1-yloxy)phenyl]propanamid, (15.078) N-[(5-Brom-3-chlorpyridin-2-yl)methyl]-2,4-dichlomicotinamid, (15.079) N-[1-(5-Brom-3-chlorpyridin-2-yl)ethyl]-2,4-dichlornicotinamid, (15.080) N-[1-(5-Brom-3-chlorpyridin-2-yl)ethyl]-2-fluor-4-iodnicotinamid, (15.081) N- {(E)-[(Cyclopropylmethoxy)imino][6-(difluormethoxy)-2,3-difluorphenyl]methyl}-2-phenylacetamid, (15.082) N-{(Z)-[(Cyclopropylmethoxy)imino][6-(difluormethoxy)-2,3-difluorphenyl]methyl}-2-phenylacetamid, (15.083) N'-{4-[(3-tert.-Butyl-4-cyano-1,2-thiazol-5-yl)oxy]-2-chlor-5-methylphenyl}-N-ethyl-N-methylimidoformamid, (15.084) N-Methyl-2-(1-{[5-methyl-3-(trifluormethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-(1,2,3,4-tetrahydronaphthalin-1-yl)-1,3-thiazol-4-carboxamid, (15.085) N-Methyl-2-(1-{[5-methyl-3-(trifluormethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1R)-1,2,3,4-tetrahydronaphthalin-1-yl]-1,3-thiazol-4-carboxamid, (15.086) N-Methyl-2-(1-{[5-methyl-3-(trifluormethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1S)-1,2,3,4-tetrahydronaphthalin-1-yl]-1,3-thiazol-4-carboxamid, (15.087) {6-[({[(1-Methyl-1H-tetrazol-5-yl)(phenyl)methylen]amino}oxy)methyl]pyridin-2-yl}¬carbamidsäurepentylester, (15.088) Phenazin-1 -carbonsäure, (15.089) Chinolin-8-ol, (15.090) Chinolin-8-olsulfat (2:1), (15.091) {6-[({[(1-Methyl-1H-tetrazol-5-yl)(phenyl)methylen]¬ammo}¬oxy)methyl]pyridin-2-yl}carbamidsäure-tert.-butylester, (15.092) (5-Brom-2-methoxy-4-methyl-pyridin-3-yl)(2,3,4-trimethoxy-6-methylphenyl)methanon, (15.093) N-[2-(4-{[3-(4-Chlorphenyl)prop-2-in-1-yl]oxy}-3-methoxyphenyl)ethyl]-N2-(methylsulfonyl)valinamid, (15.094) 4-Oxo-4-[(2-phenylethyl)amino]butansäure, (15.095) {6-[({[(Z)-(1-Methyl-1H-tetrazol-5-yl)(phenyl)methylen]¬amino}oxy)methyl]pyridin-2-yl}carbamidsäurebut-3-in-1-ylester, (15.096) 4-Amino-5-fluor-pyrimidin-2-ol (tautomere Form: 4-Amino-5-fluorpyrimidin-2(1H)-on), (15.097) 3,4,5-Trihydroxybenzoesäurepropylester, (15.098) [3-(4-Chlor-2-fluorphenyl)-5-(2,4-difluorphenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (15.099) (S)-[3-(4-Chlor-2-fluorphenyl)-5-(2,4-difluorphenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (15.100) (R)-[3-(4-Chlor-2-fluorphenyl)-5-(2,4-difluorphenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (15.101) 2-Fluor-6-(trifluormethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)benzamid, (15.102) 2-(6-Benzylpyridin-2-yl)chinazolin, (15.103) 2-[6-(3-Fluor-4-methoxyphenyl)-5-methylpyridin-2-yl]chinazolin, (15.104) 3-(4,4-Difluor-3,3-dimethyl-3,4-dihydroisochinolin-1-yl)chinolin, (15.105) Abscisinsäure, (15.106) N'-[5-Brom-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidoformamid, (15.107) N'- {5-Brom-6-[1-(3,5-difluorphenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamid, (15.108) N'-{5-Brom-6-[(1R)-1-(3,5-difluorphenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamid, (15.109) N'-{5-Brom-6-[(1S)-1-(3,5-difluorphenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamid, (15.110) N'-{5-Brom-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamid, (15.111) N'-{5-Brom-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamid, (15.112) N-Cyclopropyl-3-(difluormethyl)-5-fluor-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazol-4-carboxamid, (15.113) N-Cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluormethyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (15.114) N-(2-tert.-Butylbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (15.115) N-(5-Chlor-2-ethylbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (15.116) N-(5-Chlor-2-isopropylbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (15.117) N-Cyclopropyl-3-(difluormethyl)-N-(2-ethyl-5-fluorbenzyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (15.118) N-Cyclopropyl-3-(difluormethyl)-5-fluor-N-(5-fluor-2-isopropylbenzyl)-1-methyl-1H-pyrazol-4-carboxamid, (15.119) N-Cyclopropyl-N-(2-cyclopropyl-5-fluorbenzyl)-3-(difluormethyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (15.120) N-(2-Cyclopentyl-5-fluorbenzyl)-N-cyclopropyl-3 -(difluormethyl)-5 -fluor-1 -methyl-1H-pyrazol-4-carboxamid, (15.121) N-Cyclopropyl-3-(difluormethyl)-5-fluor-N-(2-fluor-6-isopropylbenzyl)-1-methyl-1H-pyrazol-4-carboxamid, (15.122) N-Cyclopropyl-3-(difluormethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (15.123) N-Cyclopropyl-3-(difluormethyl)-5-fluor-N-(2-isopropyl-5-methylbenzyl)-1-methyl-1H-pyrazol-4-carboxamid, (15.124) N-Cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluormethyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (15.125) N-(2-tert.-Butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (15.126) N-[5-Chlor-2-(trifluormethyl)benzyl]-N-cyclopropyl-3-(difluormethyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (15.127) N-Cyclopropyl-3-(difluormethyl)-5-fluor-1-methyl-N-[5-methyl-2-(trifluormethyl)benzyl]-1H-pyrazol-4-carboxamid, (15.128) N-[2-Chlor-6-(trifluormethyl)benzyl] -N-cyclopropyl-3-(difluormethyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (15.129) N-[3-Chlor-2-fluor-6-(trifluormethyl)benzyl]-N-cyclopropyl-3-(difluormethyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (15.130) N-Cyclopropyl-3-(difluormethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (15.131) N-Cyclopropyl-3-(difluormethyl)-5-fluor-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazol-4-carbothioamid, (15.132) N'-(2,5-Dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamid, (15.133) N'-{4-[(4,5-Dichlor-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamid, (15.134) N-(4-Chlor-2,6-difluorphenyl)-4-(2-chlor-4-fluorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (15.135) 9-Fluor-2,2-dimethyl-5-(chinolin-3-yl)-2,3-dihydro-1,4-benzoxazepin, (15.136) 2-{2-Fluor-6-[(8-fluor-2-methylchinolin-3-yl)oxy]phenyl}propan-2-ol, (15.137) 2-{2-[(7,8-Difluor-2-methylchinolin-3-yl)oxy]-6-fluorphenyl}propan-2-ol, (15.138) 4-(2-Chlor-4-fluorphenyl)-N-(2-fluorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (15.139) 4-(2-Chlor-4-fluorphenyl)-N-(2,6-difluorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (15.140) 4-(2-Chlor-4-fluorphenyl)-N-(2-chlor-6-fluorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (15.141) 4-(2-Brom-4-fluorphenyl)-N-(2-chlor-6-fluorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (15.142) N-(2-Brom-6-fluorphenyl)-4-(2-chlor-4-fluorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (15.143) 4-(2-Brom-4-fluorphenyl)-N-(2-bromphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (15.144) 4-(2-Brom-4-fluorphenyl)-N-(2-brom-6-fluorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (15.145) 4-(2-Brom-4-fluorphenyl)-N-(2-chlorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (15.146) N-(2-Bromphenyl)-4-(2-chlor-4-fluorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (15.147) 4-(2-Chlor-4-fluorphenyl)-N-(2-chlorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (15.148) 4-(2-Brom-4-fluorphenyl)-N-(2,6-difluorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (15.149) 4-(2-Brom-4-fluorphenyl)-N-(2-fluorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (15.150) N'-(4- {3-[(Difluormethyl)sulfanyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamid, (15.151) N'-(2,5-Dimethyl-4-{3-[(1,1,2,2-tetrafluorethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamid, (15.152) N'-(2,5-Dimethyl-4- {3-[(2,2,2-trifluorethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamid, (15.153) N'-(2,5-Dimethyl-4-{3-[(2,2,3,3-tetrafluorpropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamid, (15.154) N'-(2,5-Dimethyl-4-{3-[(pentafluorethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamid, (15.155) N'-(4-{[3-(Difluormethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamid, (15.156) N'-(2,5-Dimethyl-4-{[3-(1,1,2,2-tetrafluorethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamid, (15.157) N'-(2,5-Dimethyl-4-{[3-(2,2,2-trifluorethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamid, (15.158) N'-(2,5-Dimethyl-4-{[3-(2,2,3,3-tetrafluorpropoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamid, (15.159) N'-(2,5-Dimethyl-4-{[3-(pentafluorethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamid, (15.160) 2-[3,5-Bis(difluormethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-(prop-2-in-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanon, (15.161) 2-[3,5-Bis(difluormethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-fluor-6-(prop-2-in-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanon, (15.162) 2-[3,5-Bis(difluormethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-chlor-6-(prop-2-in-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanon, (15.163) 2-{3-[2-(1-{[3,5-Bis(difluormethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenylmethansulfonat, (15.164) 2-{3-[2-(1-{[3,5-Bis(difluormethyl)-1H-pyrazol-1-yl]¬acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorphenylmethansulfonat, (15.165) 2-[3,5-Bis(difluormethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5S)-5-[2-(prop-2-in-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanon, (15.166) 2-[3,5-Bis(difluormethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5R)-5-[2-(prop-2-in-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanon, (15.167) 2-[3,5-Bis(difluormethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5S)-5-[2-fluor-6-(prop-2-in-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanon, (15.168) 2-[3,5-Bis(difluormethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5R)-5-[2-fluor-6-(prop-2-in-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanon, (15.169) 2-[3,5-Bis(difluormethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5S)-5-[2-chlor-6-(prop-2-in-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanon, (15.170) 2-[3,5-Bis(difluormethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5R)-5-[2-chlor-6-(prop-2-in-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanon, (15.171) 2-{(5S)-3-[2-(1-{[3,5-Bis(difluormethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenylmethansulfonat, (15.172) 2-{(5R)-3-[2-(1-{[3,5-Bis(difluormethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenylmethansulfonat, (15.173) 2-{(5S)-3-[2-(1-{[3,5-Bis(difluormethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorphenylmethansulfonat, (15.174) 2-{(5R)-3-[2-(1-{[3,5-Bis(difluormethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorphenylmethansulfonat.
All listed fungicidal mixing partners of classes (1) to (15) can optionally form salts with corresponding bases or acids, provided that suitable functional groups are present. In addition, tautomeric forms are also included for the listed fungicidal mixing partners of classes (1) to (15), provided that tautomerism is possible.
  1. 1) inhibitors of ergosterol biosynthesis, for example (1.01) aldimorph, (1.02) azaconazole, (1.03) bitertanol, (1.04) bromuconazole, (1.05) cyproconazole, (1.06) diclobutrazole, (1.07) difenoconazole, (1.08) diniconazole, (1.09 ) Dinemonazole-M, (1.10) dodemorph, (1.11) dodemorphoacetate, (1.12) epoxiconazole, (1.13) etaconazole, (1.14) fenarimol, (1.15) fenbuconazole, (1.16) fenhexamid, (1.17) fenpropidin, (1.18) fenpropimorph, (1.19) fluquinconazole, (1.20) flurprimidol, (1.21) flusilazole, (1.22) flutriafol, (1.23) furconazole, (1.24) furconazole-cis, (1.25) hexaconazole, (1.26) imazalil, (1.27) imazalil sulfate, (1.28) Imibenconazole, (1.29) ipconazole, (1.30) metconazole, (1.31) myclobutanil, (1.32) naftifine, (1.33) nuarimol, (1.34) oxpoconazole, (1.35) paclobutrazole, (1.36) pefurazoate, (1.37) penconazole, (1.38) Piperaline, (1.39) prochloroconazole, (1.42) propiconazole, (1.41) pyributicarb, (1.43) pyrifenox, (1.44) quinconazole, (1.45) simeconazole, (1.46) spiroxamine, (1.47) tebuconazole, (1 .48) Terbinafine, (1.49) Tetraconazole, (1.50) Triadimefon, (1.51) Triadimenol, (1.52) Tridemorph, (1.53) Triflumizole, (1.54) Triforin, (1.55) Triticonazole, (1.56) Uniconazole, (1.57) Uniconazole p, (1.58) viniconazole, (1.59) voriconazole, (1.60) 1- (4-chlorophenyl) -2- (1H-1,2,4-triazol-1-yl) cycloheptanol, (1.61) 1- (2, 2-Dimethyl-2,3-dihydro-1H-inden-1-yl) -1H-imidazole-5-carboxylic acid methyl ester, (1.62) N '- {5- (difluoromethyl) -2-methyl-4- [3- ( trimethylsilyl) propoxy] phenyl} -N-ethyl-N-methylimidoformamide, (1.63) N -ethyl-N-methyl-N '- {2-methyl-5- (trifluoromethyl) -4- [3- (trimethylsilyl) propoxy] phenyl} imidoformamide, (1.64) O- [1- (4-methoxyphenoxy) -3,3-dimethylbutan-2-yl] -1H-imidazole-1-carbothioate, (1.65) pyrisoxazole, (1.66) 2 - {[3 - (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.67) 1- {[3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H-1,2,4-triazol-5-ylthiocyanat, (1.68) 5- (Allylsulfanyl) -1 - {[3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H-1,2,4-triazole, 1.69) 2- [1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-1,2,4-triazole-3 thion, (1.70) 2 - {[rel (2R, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -2,4-dihydro-3H- 1,2,4-triazole-3-thione, (1.71) 2 - {[rel (2R, 3R) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.72) 1 - {[rel (2R, 3S) -3- (2-chlorophenyl) -2- (2, 4-difluorophenyl) oxiran-2-yl] methyl} -1H-1,2,4-triazol-5-yl thiocyanate, (1.73) 1 - {[rel (2R, 3R) -3- (2-chlorophenyl) -2 - (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H-1,2,4-triazol-5-yl thiocyanate, (1.74) 5- (allylsulfanyl) -1 - {[rel (2R, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H-1,2,4-triazole, (1.75) 5- (allylsulfanyl) -1 - {[ rel (2R, 3R) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H-1,2,4-triazole, (1.76) 2 - [( 2S, 4S, 5S) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptane-4-yl] -2,4- dihydro-3H-1,2,4-triazole-3-thione, (1.77) 2 - [(2R, 4S, 5S) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6- trimethylheptan-4-yl] -2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.78) 2 - [(2R, 4R, 5R) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.79) 2 - [(2S, 4R, 5R ) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-1,2,4-triazole-3-thione, 1.80) 2 - [(2S, 4S, 5R) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-1, 2,4-triazole-3-thione, (1.81) 2 - [(2R, 4S, 5R) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.82) 2 - [(2R, 4R, 5S) -1- (2,4-dichlorophenyl) -5-hydroxy-2 , 6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.83) 2 - [(2S, 4R, 5S) -1- (2 , 4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.84) 2- [4 - (4-chlorophenoxy) -2- (trifluoromethyl) phenyl] -1- (1H-1,2,4-triazol-1-yl) -propan-2-ol, (1.85) 2- [4- (4-chlorophenoxy ) -2- (trifluoro methyl) phenyl] -1- (1H-1,2,4-triazol-1-yl) butan-2-ol, (1.86) 2- [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl] - 1- (1H-1,2,4-triazol-1-yl) -pentan-2-ol, (1.87) 2- [2-chloro-4- (4-chlorophenoxy) phenyl] -1- (1H-1, 2,4-triazol-1-yl) butan-2-ol, (1.88) 2- [2-chloro-4- (2,4-dichlorophenoxy) phenyl] -1- (1H-1,2,4-triazole -1-yl) propan-2-ol, (1.89) (2R) -2- (1-chlorocyclopropyl) -4 - [(1R) -2,2-dichlorocyclopropyl] -1- (1H-1,2,4 -triazol-1-yl) butan-2-ol, (1.90) (2R) -2- (1-chlorocyclopropyl) -4 - [(1S) -2,2-dichlorocyclopropyl] -1- (1H-1,2 , 4-triazol-1-yl) butan-2-ol, (1.91) (2S) -2- (1-chlorocyclopropyl) -4 - [(1S) -2,2-dichlorocyclopropyl] -1- (1H-1 , 2,4-triazol-1-yl) butan-2-ol, (1.92) (2S) -2- (1-chlorocyclopropyl) -4 - [(1R) -2,2-dichlorocyclopropyl] -1- (1H 1,2,4-triazol-1-yl) butan-2-ol, (1.93) (1S, 2R, 5R) -5- (4-chlorobenzyl) -2- (chloromethyl) -2-methyl-1 (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol, (1.94) (1R, 2S, 5S) -5- (4-chlorobenzyl) -2- (chloromethyl) -2-methyl-1- (1H -1,2,4-triazol-1-ylmethyl) cyclopentanol, (1.95) 5- (4-chlorobenzyl) -2- (chloromethyl) -2-methyl-1- (1H-1,2 , 4-triazol-1-ylmethyl) cyclopentanol.
  2. 2) inhibitors of the respiratory chain on complex I or II, for example (2.01) bixafen, (2.02) boscalid, (2.03) carboxin, (2.04) difluorotorim, (2.05) fenfuram, (2.06) fluopyram, (2.07) flutolanil, (2.08 ) Fluxapyroxad, (2.09) Furametpyr, (2.10) Furmecyclox, (2.11) Isopyrazam (mixture of syn-epimeric racemate 1RS, 4SR, 9RS and anti-epimeric racemate 1RS, 4SR, 9SR), (2.12) isopyrazam (anti-epimeric Racemate 1RS, 4SR, 9SR), (2.13) isopyrazam (anti-epimeric enantiomer 1R, 4S, 9S), (2.14) isopyrazam (anti-epimeric enantiomer 1S, 4R, 9R), (2.15) isopyrazam (syn-epimeric racemate 1RS , 4SR, 9RS), (2.16) isopyrazam (syn-epimeric enantiomer 1R, 4S, 9R), (2.17) isopyrazam (syn-epimeric enantiomer 1S, 4R, 9S), (2.18) mepronil, (2.19) oxycarboxine, (2.20 ) Penflufen, (2.21) Penthiopyrad, (2.22) Sedaxane, (2.23) Thifluzamide, (2.24) 1-Methyl-N- [2- (1,1,2,2-tetrafluoroethoxy) phenyl] -3- (trifluoromethyl) - 1H-pyrazole-4-carboxamide, (2.25) 3- (difluoromethyl) -1-methyl-N- [2- (1,1,2,2-tetrafluoroethoxy) phenyl] -1H-pyrazole-4-carboxamide, (2.26 ) 3- (Difluoromethyl) -N- [4-fluoro-2- (1,1,2,3,3,3-hexafluoropropoxy) phenyl] -1-methyl-1H-pyrazole-4-carboxamide, (2.27) N - [1- (2,4-dichlorophenyl) -1-methoxy-propan-2-yl] -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, (2.28) 5,8-difluoro-N- [2- (2-fluoro-4 - {[4- (trifluoromethyl) pyridin-2-yl] oxy} phenyl) ethyl] quinazolin-4-amine, (2.29) benzovindiflupyr, (2.30) N - [(1S, 4R ) -9- (dichloromethylene) -1,2,3,4-Tetrah ydro-1,4-methanonaphthalen-5-yl] -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, (2.31) N - [(1R, 4S) -9- (dichloromethylene) -1 , 2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl] -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, (2.32) 3- (difluoromethyl) -1-methyl -N- (1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl) -1H-pyrazole-4-carboxamide, (2.33) 1,3,5-trimethyl-N- (1 , 1,3-trimethyl-2,3-dihydro-1H-inden-4-yl) -1H-pyrazole-4-carboxamide, (2.34) 1-methyl-3- (trifluoromethyl) -N- (1,1, 3-trimethyl-2,3-dihydro-1H-inden-4-yl) -1H-pyrazole-4-carboxamide, (2.35) 1-methyl-3- (trifluoromethyl) -N - [(3R) -1,1 , 3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide, (2.36) 1-methyl-3- (trifluoromethyl) -N - [(3S) -1, 1,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide, (2.37) 3- (difluoromethyl) -1-methyl-N - [(3S) -1 , 1,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide, (2.38) 3- (difluoromethyl) -1-methyl-N - [(3R) - 1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide, (2.39) 1,3,5-trimethyl-N - [(3R) - 1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide, (2.40) 1,3,5-trimethyl-N - [(3S) -1 , 1,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide, (2.41) benodanil, (2.42) 2-chloro-N- (1,1,3 -trimethyl-2,3-dihydro-1H-inden-4-yl) pyridine-3-carboxamide, (2.43) isofetamide, (2.44) 1-methyl-3- (trifluoromethyl) -N- [2 '- (trifluoromethyl) biphenyl-2-yl] -1H-pyrazole-4-carboxamide, (2.45) N- (4'-chlorobiphenyl-2-yl) -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, ( 2.46) N- (2 ', 4'-dichlorobiphenyl-2-yl) -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, (2.47) 3- (difluoromethyl) -1-methyl-N - [4 '- (trifluoromethyl) biphenyl-2-yl] -1H-pyrazole-4-carboxamide, (2.48) N- (2', 5'-difluorobiphenyl-2-yl) -1-methyl-3- (trifluoromethyl ) -1H-pyrazole-4-carboxamide, (2.49) 3- (difluoromethyl) -1-methyl-N- [4 '- (prop-1-yn-1-yl) biphenyl-2-yl] -1H-pyrazole 4-carboxamide, (2.50) 5-fluoro-1,3-dimethyl-N- [4 '- (prop-1-yn-1-yl) biphenyl-2-yl] -1H-pyrazole-4-carboxamide, (2.51) 2-Chloro-N- [4 '- (prop-1-yn-1-yl) biphenyl-2-yl] nicotinamide, (2.52 ) 3- (Difluoromethyl) -N- [4 '- (3,3-dimethylbut-1-yn-1-yl) biphenyl-2-yl] -1-methyl-1H-pyrazole-4-carboxamide, (2.53) N- [4 '- (3,3-dimethylbut-1-yn-1-yl) biphenyl-2-yl] -5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide, (2.54) 3 (Difluoromethyl) -N- (4'-ethynyl-biphenyl-2-yl) -1-methyl-1H-pyrazole-4-carboxamide, (2.55) N- (4'-ethynyl-biphenyl-2-yl) -5-fluoro 1,3-dimethyl-1H-pyrazole-4-carboxamide, (2.56) 2-chloro-N- (4'-ethynyl-biphenyl-2-yl) nicotinamide, (2.57) 2-chloro-N- [4 '- (3 , 3-dimethylbut-1-yn-1-yl) biphenyl-2-yl] nicotinamide, (2.58) 4- (difluoromethyl) -2-methyl-N- [4 '- (trifluoromethyl) biphenyl-2-yl] - 1,3-thiazole-5-carboxamide, (2.59) 5-fluoro-N- [4 '- (3-hydroxy-3-methylbut-1-yn-1-yl) biphenyl-2-yl] -1,3 dimethyl-1H-pyrazole-4-carboxamide, (2.60) 2-Chloro-N- [4 '- (3-hydroxy-3-methylbut-1-yn-1-yl) biphenyl-2-yl] nicotinamide, (2.61) 3- (difluoromethyl) -N- [ 4 '- (3-methoxy-3-methylbut-1-yn-1-yl) biphenyl-2-yl] -1-methyl-1H-pyrazole-4-carboxamide, (2.62) 5-fluoro-N- [4 '- (3-methoxy-3-methylbut-1-yn-1-yl) biphenyl-2-yl] -1,3-dimethyl-1H-pyrazole-4-carboxamide, (2.63) 2-chloro-N- [ 4 '- (3-methoxy-3-methylbut-1-yn-1-yl) biphenyl-2-yl] nicotinamide, (2.64) 1,3-dimethyl-N- (1,1,3-trimethyl-2, 3-dihydro-1H-inden-4-yl) -1H-pyrazole-4-carboxamide, (2.65) 1,3-dimethyl-N - [(3R) -1,1,3-trimethyl-2,3-dihydro -1H-inden-4-yl] -1H-pyrazole-4-carboxamide, (2.66) 1,3-dimethyl-N - [(3S) -1,1,3-trimethyl-2,3-dihydro-1H- inden-4-yl] -1H-pyrazole-4-carboxamide, (2.67) 3- (difluoromethyl) -N-methoxy-1-methyl-N- [1- (2,4,6-trichlorophenyl) -propane-2-one] yl] -1H-pyrazole-4-carboxamide, (2.68) 3- (difluoromethyl) -N- (7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl) - 1-methyl-1H-pyrazole-4-carboxamide, (2.69) 3- (difluoromethyl) -N - [(3R) -7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-indene 4-yl] -1-methyl-1H-pyrazol-4-CarbOxa mid, (2.70) 3- (difluoromethyl) -N - [(3S) -7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1-methyl-1H pyrazole-4-carboxamide.
  3. 3) Complex III respiratory chain inhibitors, for example (3.01) ametoctradine, (3.02) amisulbrom, (3.03) azoxystrobin, (3.04) cyazofamide, (3.05) coumethoxystrobin, (3.06) coumoxystrobin, (3.07) dimoxystrobin, (3.08) enoxastrobin , (3.09) famoxadone, (3.10) fenamidone, (3.11) flufenoxystrobin, (3.12) fluoxastrobin, (3.13) kresoxim-methyl, (3.14) metominostrobin, (3.15) orysastrobin, (3.16) picoxystrobin, (3.17) pyraclostrobin, (3.18 ) Pyrametostrobin, (3.19) Pyraoxystrobin, (3.20) Pyribencarb, (3.21) Triclopyricarb, (3.22) Trifloxystrobin, (3.23) (2E) -2- (2 - {[6- (3-Chloro-2-methylphenoxy) -5 -fluoropyrimidin-4-yl] oxy} phenyl) -2- (methoxyimino) -N-methylacetamide, (3.24) (2E) -2- (methoxyimino) -N-methyl-2- (2 - {[({ (1E) -1- [3- (trifluoromethyl) phenyl] ethylidene (amino) oxy] methyl} phenyl) acetamide, (3.25) (2E) -2- (methoxyimino) -N-methyl-2- {2- [(E) - ({1- [3- (trifluoromethyl) phenyl] ethoxy} imino) methyl] phenyl} acetamide, (3.26) (2E) -2- {2 - [({[(1E) -1- ( 3 - {[(e) -1-fluoro-2-phenylvinyl] oxy} phenyl) ethylidene] amino} oxy) methyl l] phenyl} -2- (methoxyimino) -N-methylacetamide, (3.27) fenaminostrobin, (3.28) 5-methoxy-2-methyl-4- (2 - {[({(1E) -1- [3- (3) trifluoromethyl) phenyl] ethylidene} amino) oxy] methyl} phenyl) -2,4-dihydro-3H-1,2,4-triazol-3-one, (3.29) (2E) -2- {2 - [({ Cyclopropyl [(4-methoxyphenyl) imino] methyl} sulfanyl) methyl] phenyl} -3-methoxyacrylate, (3.30) N- (3-ethyl-3,5,5-trimethylcyclohexyl) -3-formamido-2-hydroxybenzamide, 3.31) 2- {2 - [(2,5-dimethylphenoxy) methyl] phenyl} -2-methoxy-N-methylacetamide, (3.32) 2- {2 - [(2,5-dimethylphenoxy) methyl] phenyl} -2 -methoxy-N-methylacetamide, (3.33) (2E, 3Z) -5 - {[1- (4-chlorophenyl) -1H-pyrazol-3-yl] oxy} -2- (methoxyimino) -N, 3-dimethylpent -3-enamide.
  4. 4) inhibitors of mitosis and cell division, for example (4.01) benomyl, (4.02) carbendazim, (4.03) chlorfenazole, (4.04) diethofencarb, (4.05) ethaboxam, (4.06) fluopicolide, (4.07) fuberidazole, (4.08) pencycuron, (4.09) thiabendazole, (4.10) thiophanate-methyl, (4.11) thiophanate, (4.12) zoxamide, (4.13) 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6- trifluorophenyl) [1,2,4] triazolo [1,5-a] pyrimidine, (4.14) 3-chloro-5- (6-chloropyridin-3-yl) -6-methyl-4- (2,4,6 trifluorophenyl) pyridazine.
  5. 5) compounds capable of attacking at multiple sites ("multisite action"), for example (5.01) Bordeaux mixture, (5.02) captafol, (5.03) captan, (5.04) chlorothalonil, (5.05) copper hydroxide, ( 5.06) copper naphthenate, (5.07) copper oxide, (5.08) copper oxychloride, (5.09) copper (2+) sulfate, (5.10) dichlorofluanide, (5.11) dithianon, (5.12) dodin, (5.13) dodine free base, (5.14) Ferbam, (5.15) fluorofolpet, (5.16) folpet, (5.17) guazatine, (5.18) guazatine acetate, (5.19) iminoctadine, (5.20) iminoctadinalbesilate, (5.21) iminoctadine triacetate, (5.22) mancopper, (5.23) mancozeb, (5.24) Maneb, (5.25) metiram, (5.26) metiram-zinc, (5.27) oxine-copper, (5.28) propamidine, (5.29) propineb, (5.30) sulfur and sulfur compounds including calcium polysulfide, (5.31) thiram, (5.32) tolylfluanid, (5.33) zineb, (5.34) ziram, (5.35) anilazine.
  6. 6) Compounds capable of inducing host defense response, for example (6.01) acibenzolar-S-methyl, (6.02) isotianil, (6.03) probenazole, (6.04) tiadinil, (6.05) laminarin.
  7. 7) inhibitors of amino acid and / or protein biosynthesis, for example (7.01) andoprim, (7.02) blasticidin-S, (7.03) cyprodinil, (7.04) kasugamycin, (7.05) kasugamycin hydrochloride hydrate, (7.06) mepanipyrim, (7.07) Pyrimethanil, (7.08) 3- (5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl) quinoline, (7.09) oxytetracycline, (7.10) streptomycin.
  8. 8) inhibitors of ATP production, for example (8.01) fentin acetate, (8.02) fentin chloride, (8.03) fentin hydroxide, (8.04) silthiofam.
  9. 9) inhibitors of cell wall synthesis, for example (9.01) benthi- avalicarb, (9.02) dimethomorph, (9.03) flumorph, (9.04) iprovalicarb, (9.05) mandipropamide, (9.06) polyoxines, (9.07) polyoxorim, (9.08) validamycin A, ( 9.09) Valifenalate, (9.10) Polyoxin B, (9.11) (2E) -3- (4-tert-butylphenyl) -3- (2-chloropyridin-4-yl) -1- (morpholin-4-yl) prop -2-en-1-one, (9.12) (2Z) -3- (4-tert-butylphenyl) -3- (2-chloropyridin-4-yl) -1- (morpholin-4-yl) propyl 2-en-1-one.
  10. 10) inhibitors of lipid and membrane synthesis, for example (10.01) biphenyl, (10.02) chloroneb, (10.03) diclorane, (10.04) edifenphos, (10.05) etridiazole, (10.06) iodocarb, (10.07) Iprobenfos, (10.08) isoprothiolane , (10.09) Propamocarb, (10.10) Propamocarb hydrochloride, (10.11) Prothiocarb, (10.12) Pyrazophos, (10.13) Quintozene, (10.14) Tecnazene, (10.15) Tolclofos-methyl.
  11. 11) inhibitors of melanin biosynthesis, for example (11.01) carpropamide, (11.02) diclocymet, (11.03) fenoxanil, (11.04) phthalide, (11.05) pyroquilone, (11.06) tricyclazole, (11.07) 2,2,2-trifluoroethyl {3 -methyl-1 - carbamate [(4-methylbenzoyl) amino] butan-2-yl}.
  12. 12) Inhibitors of Nucleic Acid Synthesis, for example (12.01) Benalaxyl, (12.02) Benalaxyl-M (Kiralaxyl), (12.03) Bupirimat, (12.04) Clozylacone, (12.05) Dimethirimol, (12.06) Ethirimol, (12.07) Furalaxyl, (12.08 ) Hymexazole, (12.09) Metalaxyl, (12.10) Metalaxyl-M (mefenoxam), (12.11) Ofurace, (12.12) Oxadixyl, (12.13) Oxolinic acid, (12.14) Octhilinone.
  13. 13) inhibitors of signal mediation, for example (13.01) chlozolinate, (13.02) fenpiclonil, (13.03) fludioxonil, (13.04) iprodione, (13.05) procymidone, (13.06) quinoxyfen, (13.07) vinclozoline, (13.08) proquinazide.
  14. 14) compounds which may act as decouplers, for example (14.01) binapacryl, (14.02) dinocap, (14.03) ferimzone, (14.04) fluazinam, (14.05) meptyldinocap.
  15. 15) Further compounds, for example (15.001) Benthiazole, (15.002) Bethoxazine, (15.003) Capsimycin, (15.004) Carvone, (15.005) Quinomethionate, (15.006) Pyriofenone (Chlazafenone), (15.007) Cufraneb, (15.008) Cyflufenamid, (15.009) Cymoxanil, (15.010) Cyprosulfamide, (15.011) Dazomet, (15.012) Debacarb, (15.013) Dichlorophene, (15.014) Diclomecine, (15.015) Difenzoquat, (15.016) Difenzoquatmetyl sulfate, (15.017) Diphenylamine, (15.018) Ecomat, (15.019) fenpyrazamine, (15.020) flumetover, (15.021) fluoroimide, (15.022) flusulfamide, (15.023) flutianil, (15.024) fosetyl-aluminum, (15.025) fosetyl-calcium, (15.026) fosetyl-sodium, (15.027) hexachlorobenzene , (15,028) Irumamycin, (15,029) Methasulfocarb, (15,030) Methyl isothiocyanate, (15,031) Metrafenone, (15,032) Mildiomycin, (15,033) Natamycin, (15,034) Nickeldimethyldithiocarbamate, (15,035) Nitrothalisopropyl, (15,036) Oxamocarb, (15,037) Oxyfenthiine , (15.038) pentachlorophenol and salts, (15.039) phenothrin, (15.040) phosphorous acid and its S alze, (15,041) propamocarb-fosetylate, (15,042) propanosine sodium, (15,043) pyrimorph, (15,044) pyrroline nitrine, (15,045) tebufloquine, (15,046) tecloftalam, (15,047) tolnifanide, (15,048) triazoxide, (15,049) trichlamide , (15,050) Zarilamide, (15,051) 2-Methylpropanoic acid (3S, 6S, 7R, 8R) -8-benzyl-3 - [({3 - [(isobutyryloxy) methoxy] -4-methoxypyridin-2-yl} carbonyl ) amino] -6-methyl-4,9-dioxo-1,5-dioxonan-7-yl ester, (15.052) 1- (4- {4 - [(5R) -5- (2,6-difluorophenyl) -] 4,5-dihydro-1,2-oxazol-3-yl] -1,3-thiazol-2-yl} piperidin-1-yl) -2- [5-methyl-3- (trifluoromethyl) -1H-pyrazol -1-yl] ethanone, (15,053) 1- (4- {4 - [(5S) -5- (2,6-difluorophenyl) -4,5-dihydro-1,2-oxazol-3-yl] - 1,3-thiazol-2-yl} piperidin-1-yl) -2- [5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] ethanone, (15.054) oxathiapiproline, (15.055) 1H- Imidazole-1-carboxylic acid 1- (4-methoxyphenoxy) -3,3-dimethylbutan-2-yl ester, (15.056) 2,3,5,6-tetrachloro-4- (methylsulfonyl) pyridine, (15,057) 2,3 Dibutyl-6-chlorothieno [2,3-d] pyrimidin-4 (3H) -one, (15,058) 2,6-dimethyl-1H, 5H- [1,4] dithiino [2, 3-c: 5,6-c '] dipyrrol-1,3,5,7 (2H, 6H) -tetrone, (15,059) 2- [5-methyl-3- (trifluoromethyl) -1H-pyrazole-1 yl] -1- (4- {4 - [(5R) -5-phenyl-4,5-dihydro-1,2-oxazol-3-yl] -1,3-thiazol-2-yl} piperidin-1 -yl) ethanone, (15.060) 2- [5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] -1- (4- {4 - [(5S) -5-phenyl-4,5 -dihydro-1,2-oxazol-3-yl] -1,3-thiazol-2-yl} piperidin-1-yl) ethanone, (15.061) 2- [5-methyl-3- (trifluoromethyl) -1H- pyrazol-1-yl] -1- {4- [4- (5-phenyl-4,5-dihydro-1,2-oxazol-3-yl) -1,3-thiazol-2-yl] piperidin-1 -yl} ethanone, (15.062) 2-butoxy-6-iodo-3-propyl-4H-chromen-4-one, (15.063) 2-chloro-5- [2-chloro-1- (2,6-difluoro 4-methoxyphenyl) -4-methyl-1H-imidazol-5-yl] pyridine, (15.064) 2-phenylphenol and salts, (15.065) 3- (4,4,5-trifluoro-3,3-dimethyl-3 , 4-dihydroisoquinolin-1-yl) quinoline, (15.066) 3,4,5-trichloropyridine-2,6-dicarboxylic acid nitrile, (15.067) 3-chloro-5- (4-chlorophenyl) -4- (2,6-) difluorophenyl) -6-methylpyridazine, (15.068) 4- (4-chlorophenyl) -5- (2,6-difluorophenyl) -3,6-dimethylpyridazine, (15,069) 5-amino-1,3,4-thiadiazole-2 -thiol, (15.07 0) 5-chloro-N'-phenyl-N '- (prop-2-yn-1-yl) thiophene-2-sulfonohydrazide, (15.071) 5-fluoro-2 - [(4-fluorobenzyl) oxy] pyrimidine 4-amine, (15,072) 5-Fluoro-2 - [(4-methylbenzyl) oxy] pyrimidin-4-amine, (15,073) 5-Methyl-6-octyl [1,2,4] triazolo [1,5-a] pyrimidine 7-amine, (15.074) (2Z) -3-amino-2-cyano-3-phenylacrylic acid ethyl ester, (15.075) N '- (4 - {[3- (4-chlorobenzyl) -1,2,4-thiadiazole] 5-yl] oxy} -2,5-dimethylphenyl) -N-ethyl-N-methylimidoformamide, (15.076) N- (4-chlorobenzyl) -3- [3-methoxy-4- (prop-2-yn-1 -yloxy) phenyl] propanamide, (15.077) N - [(4-chlorophenyl) (cyano) methyl] -3- [3-methoxy-4- (prop-2-yn-1-yloxy) phenyl] propanamide, (15.078 ) N - [(5-Bromo-3-chloro-pyridin-2-yl) methyl] -2,4-dichlomicotinamide, (15.079) N- [1- (5-bromo-3-chloro-pyridin-2-yl) -ethyl] - 2,4-dichloronicotinamide, (15.080) N- [1- (5-bromo-3-chloropyridin-2-yl) ethyl] -2-fluoro-4-iodo-nicotinamide, (15.081) N- {(E) - [( Cyclopropylmethoxy) imino] [6- (difluoromethoxy) -2,3-difluorophenyl] methyl} -2-phenylacetamide, (15,082) N - {(Z) - [(cyclopropylmethoxy) imino] [6- (difluoromethoxy) -2,3 -difluorophenyl] methyl} -2-phenylacetamide, (15.083) N '- {4 - [(3-tert-butyl-4-cyano-1,2-thiazol-5-yl) oxy] -2-chloro-5 methylphenyl} -N-ethyl-N -methylimidoformamide, (15.084) N-methyl-2- (1 - {[5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] -acetyl} -piperidin-4-yl) -N- (1,2 , 3,4-tetrahydronaphthalen-1-yl) -1,3-thiazole-4-carboxamide, (15.085) N-methyl-2- (1 - {[5-methyl-3- (trifluoromethyl) -1H-pyrazole] 1-yl] acetyl} piperidin-4-yl) -N - [(1R) -1,2,3,4-tetrahydronaphthalen-1-yl] -1,3-thiazole-4-carboxamide, (15,086) N- methyl-2- (1 - {[5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] acetyl} piperidin-4-yl) -N - [(1S) -1,2,3,4 tetrahydronaphthalen-1-yl] -1,3-thiazole-4-carboxamide, (15.087) {6 - [({[(1-methyl-1H-tetrazol-5-yl) (phenyl) methylene] amino} oxy) methyl] pyridin-2-yl} -carbamic acid pentyl ester, (15.088) phenazine-1-carboxylic acid, (15.089) quinolin-8-ol, (15.090) quinoline-8-olsulfate (2: 1), (15.091) {6- [ ({[(1-Methyl-1H-tetrazol-5-yl) (phenyl) -methylene] -ammoxy} -methyl) -pyridin-2-yl} -carbamic acid tert -butyl ester, (15.092) (5-bromo- 2-methoxy-4-methylpyridin-3-yl) (2,3,4-trimethoxy-6-methylphenyl) methanone, (15.093) N- [2- (4 - {[3- (4-chlorophenyl) prop -2-in-1-yl] oxy} -3-methoxyphe nyl) ethyl] -N2- (methylsulfonyl) valinamide, (15.094) 4-oxo-4 - [(2-phenylethyl) amino] butanoic acid, (15.095) {6 - [({[(Z) - (1-methyl) 1H-tetrazol-5-yl) (phenyl) methylene] -amino} oxy) methyl] pyridin-2-yl} -carbamic acid-3-yn-1-yl ester, (15.096) 4-amino-5-fluoro-pyrimidine-2 -ol (tautomeric form: 4-amino-5-fluoropyrimidine-2 (1H) -one), (15.097) propyl 3,4,5-trihydroxybenzoate, (15,098) [3- (4-chloro-2-fluorophenyl) -5 - (2,4-difluorophenyl) -1,2-oxazol-4-yl] (pyridin-3-yl) methanol, (15.099) (S) - [3- (4-chloro-2-fluorophenyl) -5- (2,4-difluorophenyl) -1,2-oxazol-4-yl] (pyridin-3-yl) methanol, (15,100) (R) - [3- (4-chloro-2-fluorophenyl) -5- ( 2,4-difluorophenyl) -1,2-oxazol-4-yl] (pyridin-3-yl) -methanol, (15.101) 2-fluoro-6- (trifluoromethyl) -N- (1,1,3-trimethyl- 2,3-dihydro-1H-inden-4-yl) benzamide, (15.102) 2- (6-Benzylpyridin-2-yl) quinazoline, (15.103) 2- [6- (3-fluoro-4-methoxyphenyl) - 5-methylpyridin-2-yl] quinazoline, (15.104) 3- (4,4-Difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl) quinoline, (15.105) abscisic acid, (15.106) N ' - [5-bromo-6- ( 2,3-dihydro-1H-inden-2-yloxy) -2-methylpyridin-3-yl] -N-ethyl-N-methylimidoformamide, (15.107) N '- {5-bromo-6- [1- (3 , 5-difluorophenyl) ethoxy] -2-methylpyridin-3-yl} -N-ethyl-N-methylimidoformamide, (15.108) N '- {5-bromo-6 - [(1R) -1- (3,5-) difluorophenyl) ethoxy] -2-methylpyridin-3-yl} -N-ethyl-N-methylimidoformamide, (15.109) N '- {5-bromo-6 - [(1S) -1- (3,5-difluorophenyl) ethoxy ] -2-methylpyridin-3-yl} -N-ethyl-N-methylimidoformamide, (15.110) N '- {5-bromo-6 - [(cis-4-isopropylcyclohexyl) oxy] -2-methylpyridin-3-yl } -N-ethyl-N-methylimidoformamide, (15.111) N '- {5-bromo-6 - [(trans-4-isopropylcyclohexyl) oxy] -2-methylpyridin-3-yl} -N-ethyl-N-methylimidoformamide . (15.112) N-Cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (2-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide, (15.113) N-cyclopropyl-N- (2-cyclopropylbenzyl ) -3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.114) N- (2-tert-butylbenzyl) -N-cyclopropyl-3- (difluoromethyl) -5- fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.115) N- (5-chloro-2-ethylbenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole -4-carboxamide, (15,116) N- (5-Chloro-2-isopropylbenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.117) N -Cyclopropyl-3- (difluoromethyl) -N- (2-ethyl-5-fluorobenzyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.118) N-Cyclopropyl-3- (difluoromethyl) - 5-fluoro-N- (5-fluoro-2-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide, (15.119) N-cyclopropyl-N- (2-cyclopropyl-5-fluorobenzyl) -3- ( difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.120) N- (2-cyclopentyl-5-fluorobenzyl) -N-cyclopropyl-3 - (difluoromethyl) -5-fluoro-1 - methyl-1H-pyrazole-4-carboxamide, (15. 121) N-Cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (2-fluoro-6-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide, (15.122) N-cyclopropyl-3- ( difluoromethyl) -N- (2-ethyl-5-methylbenzyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.123) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (2-isopropyl-5-methylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide, (15.124) N-cyclopropyl-N- (2-cyclopropyl-5-methylbenzyl) -3- (difluoromethyl) -5-fluoro 1-methyl-1H-pyrazole-4-carboxamide, (15.125) N- (2-tert-butyl-5-methylbenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H pyrazole-4-carboxamide, (15.126) N- [5-chloro-2- (trifluoromethyl) benzyl] -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide , (15.127) N-Cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-N- [5-methyl-2- (trifluoromethyl) benzyl] -1H-pyrazole-4-carboxamide, (15.128) N- [2-Chloro-6- (trifluoromethyl) benzyl] -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.129) N- [3-chloro-2 fluoro-6- (trifluoromethyl) benzyl] -N-cyclopropyl-3- (di fluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.130) N-cyclopropyl-3- (difluoromethyl) -N- (2-ethyl-4,5-dimethylbenzyl) -5-fluoro 1-methyl-1H-pyrazole-4-carboxamide, (15.131) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (2-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carbothioamide, ( 15.132) N '- (2,5-dimethyl-4-phenoxyphenyl) -N-ethyl-N-methylimidoformamide, (15.133) N' - {4 - [(4,5-dichloro-1,3-thiazole-2-one] yl) oxy] -2,5-dimethylphenyl} -N-ethyl-N-methylimidoformamide, (15.134) N- (4-chloro-2,6-difluorophenyl) -4- (2-chloro-4-fluorophenyl) -1 , 3-dimethyl-1H-pyrazol-5-amine, (15,135) 9-fluoro-2,2-dimethyl-5- (quinolin-3-yl) -2,3-dihydro-1,4-benzoxazepine, (15,136 ) 2- {2-Fluoro-6 - [(8-fluoro-2-methyl-quinolin-3-yl) oxy] -phenyl} -propan-2-ol, (15.137) 2- {2 - [(7,8-difluoro- 2-methylquinolin-3-yl) oxy] -6-fluorophenyl} -propan-2-ol, (15.138) 4- (2-chloro-4-fluorophenyl) -N- (2-fluorophenyl) -1,3-dimethyl- 1H-pyrazol-5-amine, (15.139) 4- (2-chloro-4-fluorophenyl) -N- (2,6-difluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (15.140) 4- (2-chloro-4-fluorophenyl) -N- ( 2-chloro-6-fluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (15.141) 4- (2-bromo-4-fluorophenyl) -N- (2-chloro-6-fluorophenyl) - 1,3-dimethyl-1H-pyrazol-5-amine, (15,142) N- (2-bromo-6-fluorophenyl) -4- (2-chloro-4-fluorophenyl) -1,3-dimethyl-1H-pyrazole -5-amine, (15,143) 4- (2-bromo-4-fluorophenyl) -N- (2-bromophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (15.144) 4- (2- Bromo-4-fluorophenyl) -N- (2-bromo-6-fluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (15.145) 4- (2-bromo-4-fluorophenyl) -N- (2-chlorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (15,146) N- (2-bromophenyl) -4- (2-chloro-4-fluorophenyl) -1,3-dimethyl-1H pyrazole-5-amine, (15.147) 4- (2-Chloro-4-fluorophenyl) -N- (2-chlorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (15,148) 4- (2-bromo-4-fluorophenyl ) -N- (2,6-difluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (15.149) 4- (2-bromo-4-fluorophenyl) -N- (2-fluorophenyl) -1 , 3-dimethyl-1H-pyrazol-5-amine, (15.150) N '- (4- {3 - [(difluoromethyl) sulfanyl] phenoxy} -2,5-dimethylphenyl) -N-ethyl-N-methylimidoformamide, ( 15.151) N '- (2,5-dimethyl-4- {3 - [(1,1,2,2-tetrafluoroethyl) sulfanyl] phenoxy} phenyl) -N-ethyl-N-methylimidoformamide, (15.152) N'- (2,5-Dimethyl-4- {3 - [(2,2,2-trifluoroethyl) sulfanyl] phenoxy} phenyl) -N-ethyl-N-methylimidoformamide, (15.153) N '- (2,5-dimethyl) 4- {3 - [(2,2,3,3-tetrafluoropropyl) sulfanyl] phenoxy} phenyl) -N-ethyl-N-methylimidoformamide, (15.154) N '- (2,5-dimethyl-4- {3- [(pentafluoroethyl) sulfanyl] phenoxy} phenyl) -N-ethyl-N-methylimidoformamide, (15.155) N '- (4 - {[3- (difluoromethoxy) phenyl] sulfanyl} -2,5-dimethylphenyl) -N-ethyl N-methylimidoformamide, (15.156) N '- (2,5-dimethyl-4 - {[3- (1,1,2,2-tetrafluoroethoxy) phenyl] sulfanyl} phenyl) -N-ethyl-N-me thylimidoformamide, (15.157) N '- (2,5-Dimethyl-4 - {[3- (2,2,2-trifluoroethoxy) phenyl] sulfanyl} phenyl) -N-ethyl-N-methylimidoformamide, (15.158) N' - (2,5-Dimethyl-4 - {[3- (2,2,3,3-tetrafluoropropoxy) phenyl] sulfanyl} phenyl) -N-ethyl-N-methylimidoformamide, (15.159) N '- (2.5 -Dimethyl-4 - {[3- (pentafluoroethoxy) phenyl] sulfanyl} phenyl) -N-ethyl-N-methylimidoformamide, (15.160) 2- [3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] -1- [4- (4- {5- [2- (prop-2-in-1-yloxy) phenyl] -4,5-dihydro-1,2-oxazol-3-yl} -1,3- thiazol-2-yl) piperidin-1-yl] ethanone, (15.161) 2- [3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] -1- [4- (4- {5- 2-fluoro-6- (prop-2-in-1-yloxy) phenyl] -4,5-dihydro-1,2-oxazol-3-yl} -1,3-thiazol-2-yl) piperidin-1 -yl] ethanone, (15.162) 2- [3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] -1- [4- (4- {5- [2-chloro-6- (propyl) 2-yn-1-yloxy) phenyl] -4,5-dihydro-1,2-oxazol-3-yl} -1,3-thiazol-2-yl) piperidin-1-yl] ethanone, (15,163) 2 - {3- [2- (1 - {[3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] acetyl} piperidin-4-yl) -1,3-thiazol-4-yl] -4 , 5-dihydro-1,2-oxazol-5-yl} phenylmethansulfon at, (15.164) 2- {3- [2- (1 - {[3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] -acetyl} -piperidin-4-yl) -1,3-thiazole 4-yl] -4,5-dihydro-1,2-oxazol-5-yl} -3-chlorophenyl methanesulfonate, (15.165) 2- [3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] -1- [4- (4 - {(5 S) -5- [2- (prop-2-in-1-yloxy) phenyl] -4,5-dihydro-1,2-oxazol-3-yl} - 1,3-thiazol-2-yl) piperidin-1-yl] ethanone, (15.166) 2- [3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] -1- [4- (4- {(5R) -5- [2- (prop-2-in-1-yloxy) phenyl] -4,5-dihydro-1,2-oxazol-3-yl} -1,3-thiazol-2-yl ) piperidin-1-yl] ethanone, (15.167) 2- [3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] -1- [4- (4 - {(5S) -5- [2 fluoro-6- (prop-2-in-1-yloxy) phenyl] -4,5-dihydro-1,2-oxazol-3-yl} -1,3-thiazol-2-yl) piperidin-1- yl] ethanone, (15.168) 2- [3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] -1- [4- (4 - {(5R) -5- [2-fluoro-6-yl] (prop-2-yn-1-yloxy) phenyl] -4,5-dihydro-1,2-oxazol-3-yl} -1,3-thiazol-2-yl) -piperidin-1-yl] -ethanone, 15.169) 2- [3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] -1- [4- (4 - {(5S) -5- [2-chloro-6- (prop-2- in-1-yloxy) phenyl] -4,5-dihydro-1,2-oxazol-3-yl} -1,3-thiazole -2-yl) piperidin-1-yl] ethanone, (15.170) 2- [3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] -1- [4- (4 - {(5R) - 5- [2-chloro-6- (prop-2-in-1-yloxy) phenyl] -4,5-dihydro-1,2-oxazol-3-yl} -1,3-thiazol-2-yl) piperidin-1-yl] ethanone, (15.171) 2 - {(5S) -3- [2- (1 - {[3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] -acetyl} -piperidine-4 -yl) -1,3-thiazol-4-yl] -4,5-dihydro-1,2-oxazol-5-yl} phenylmethanesulfonate, (15.172) 2 - {(5R) -3- [2- (1 - {[3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] acetyl} piperidin-4-yl) -1,3-thiazol-4-yl] -4,5-dihydro-1,2- oxazol-5-yl} phenylmethanesulfonate, (15.173) 2 - {(5S) -3- [2- (1 - {[3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] -acetyl} -piperidine-4 -yl) -1,3-thiazol-4-yl] -4,5-dihydro-1,2-oxazol-5-yl} -3-chlorphenylmethansulfonat, (15.174) 2 - {(5R) -3- [2- (1 - {[3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] acetyl} piperidin-4-yl) -1,3- thiazol-4-yl] -4,5-dihydro-1,2-oxazol-5-yl} -3-chlorphenylmethansulfonat.

Biologische Schädlingsbekämpfungsmittel als MischungspartnerBiological pesticides as a mix partner

Die Verbindungen der Formel (I) können mit biologischen Schädlingsbekämpfungsmitteln kombiniert werden.The compounds of formula (I) may be combined with biological pesticides.

Biologische Schädlingsbekämpfungsmittel umfassen insbesondere Bakterien, Pilze, Hefen, Pflanzenextrakte, und solche Produkte, die von Mikroorganismen gebildet wurden inklusive Proteine und sekundäre Stoffwechselprodukte.Biological pesticides include, in particular, bacteria, fungi, yeasts, plant extracts, and those products formed by microorganisms, including proteins and secondary metabolites.

Biologische Schädlingsbekämpfungsmittel umfassen Bakterien wie sporenbildende Bakterien, wurzelbesiedelnde Bakterien und Bakterien, die als biologische Insektizide, Fungizide oder Nematizide wirken.Biological pesticides include bacteria such as spore-forming bacteria, root-colonizing bacteria and bacteria that act as biological insecticides, fungicides or nematicides.

Beispiele für solche Bakterien, die als biologische Schädlingsbekämpfungsmittel eingesetzt werden bzw. verwendet werden können, sind:Examples of such bacteria which can be used as biological pesticides are:

Bacillus amyloliquefaciens, Stamm FZB42 (DSM 231179), oder Bacillus cereus, insbesondere B. cereus Stamm CNCM I-1562 oder Bacillus firmus, Stamm I-1582 (Accession number CNCM I-1582) oder Bacillus pumilus, insbesondere Stamm GB34 (Accession No. ATCC 700814) und Stamm QST2808 (Accession No. NRRL B-30087), oder Bacillus subtilis, insbesondere Stamm GB03 (Accession No. ATCC SD-1397), oder Bacillus subtilis Stamm QST713 (Accession No. NRRL B-21661) oder Bacillus subtilis Stamm OST 30002 (Accession No. NRRL B-50421) Bacillus thuringiensis, insbesondere B. thuringiensis subspecies israelensis (serotype H-14), Stamm AM65-52 (Accession No. ATCC 1276), oder B. thuringiensis subsp. aizawai, insbesondere Stamm ABTS-1857 (SD-1372), oder B. thuringiensis subsp. kurstaki Stamm HD-1, oder B. thuringiensis subsp. tenebrionis Stamm NB 176 (SD-5428), Pasteuria penetrans, Pasteuria spp. (Rotylenchulus reniformis nematode)-PR3 (Accession Number ATCC SD-5834), Streptomyces microflavus Stamm AQ6121 (= QRD 31.013, NRRL B-50550), Streptomyces galbus Stamm AQ 6047 (Acession Number NRRL 30232).Bacillus amyloliquefaciens, strain FZB42 (DSM 231179), or Bacillus cereus, in particular B. cereus strain CNCM I-1562 or Bacillus firmus, strain I-1582 (Accession number CNCM I-1582) or Bacillus pumilus, especially strain GB34 (Accession no. ATCC 700814) and strain QST2808 (Accession No. NRRL B-30087), or Bacillus subtilis, especially strain GB03 (Accession No. ATCC SD-1397), or Bacillus subtilis strain QST713 (Accession No. NRRL B-21661) or Bacillus subtilis Strain OST 30002 (Accession No. NRRL B-50421) Bacillus thuringiensis, in particular B. thuringiensis subspecies israelensis (serotype H-14), strain AM65-52 (Accession No. ATCC 1276), or B. thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372), or B. thuringiensis subsp. kurstaki strain HD-1, or B. thuringiensis subsp. tenebrionis strain NB 176 (SD-5428), Pasteuria penetrans, Pasteuria spp. (Rotylenchulus reniformis nematode) -PR3 (Accession Number ATCC SD-5834), Streptomyces microflavus strain AQ6121 (= QRD 31.013, NRRL B-50550), Streptomyces galbus strain AQ 6047 (Accession Number NRRL 30232).

Beispiele für Pilze und Hefen, die als biologische Schädlingsbekämpfungsmittel eingesetzt werden bzw. verwendet werden können, sind:Examples of fungi and yeasts which can be used as biological pesticides are:

Beauveria bassiana, insbesondere Stamm ATCC 74040, Coniothyrium minitans, insbesondere Stamm CON/M/91-8 (Accession No. DSM-9660), Lecanicillium spp., insbesondere Stamm HRO LEC 12, Lecanicillium lecanii, (ehemals bekannt als Verticillium lecanii), insbesondere Stamm KV01, Metarhizium anisopliae, insbesondere Stamm F52 (DSM3884/ ATCC 90448), Metschnikowia fructicola, insbesondere Stamm NRRL Y-30752, Paecilomyces fumosoroseus (neu: Isaria fumosorosea), insbesondere Stamm IFPC 200613, oder Stamm Apopka 97 (Accesion No. ATCC 20874), Paecilomyces lilacinus, insbesondere P. lilacinus Stamm 251 (AGAL 89/030550), Talaromyces flavus, insbesondere Stamm V117b, Trichoderma atroviride, insbesondere Stamm SC1 (Accession Number CBS 122089), Trichoderma harzianum, insbesondere T. harzianum rifai T39. (Accession Number CNCM I-952).Beauveria bassiana, especially strain ATCC 74040, coniothyrium minitans, in particular strain CON / M / 91-8 (Accession No. DSM-9660), Lecanicillium spp., In particular strain HRO LEC 12, Lecanicillium lecanii, (formerly known as Verticillium lecanii), in particular strain KV01, Metarhizium anisopliae, in particular strain F52 (DSM3884 / ATCC 90448), Metschnikowia fructicola, in particular strain NRRL Y-30752, Paecilomyces fumosoroseus (new: Isaria fumosorosea), in particular strain IFPC 200613, or strain Apopka 97 (Accesion No. ATCC 20874), Paecilomyces lilacinus, in particular P. lilacinus strain 251 (AGAL 89/030550), Talaromyces flavus, in particular strain V117b, Trichoderma atroviride, in particular strain SC1 (Accession Number CBS 122089), Trichoderma harzianum, in particular T. harzianum rifai T39. (Accession Number CNCM I-952).

Beispiele für Viren, die als biologische Schädlingsbekämpfungsmittel eingesetzt werden bzw. verwendet werden können, sind:Examples of viruses that can be used or used as biological pesticides are:

Adoxophyes orana (Apfelschalenwickler) Granulosevirus (GV), Cydia pomonella (Apfelwickler) Granulosevirus (GV), Helicoverpa armigera (Baumwollkapselwurm) Nuklear Polyhedrosis Virus (NPV), Spodoptera exigua (Zuckerrübeneule) mNPV, Spodoptera frugiperda (Heerwurm) mNPV, Spodoptera littoralis (Afrikanischer Baumwollwurm) NPV.Adoxophyes orana (Apple peel winder) Granulosis virus (GV), Cydia pomonella (codling moth) Granulosis virus (GV), Helicoverpa armigera (cotton bollworm) Nuclear polyhedrosis virus (NPV), Spodoptera exigua (mNPV), Spodoptera frugiperda (armyworm) mNPV, Spodoptera littoralis (African Cotton worm) NPV.

Es sind auch Bakterien und Pilze umfasst, die als 'Inokulant' Pflanzen oder Pflanzenteilen oder Pflanzenorganen beigegeben werden und durch ihre besonderen Eigenschaften das Pflanzenwachstum und die Pflanzengesundheit fördern. Als Beispiele sind genannt:
Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., insbesondere Burkholderia cepacia (ehemals bekannt als Pseudomonas cepacia), Gigaspora spp., oder Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., insbesondere Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp., Streptomyces spp..It also includes bacteria and fungi that are added as 'inoculant' plants or plant parts or plant organs and promote by their special properties, plant growth and plant health. Examples are:
Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., In particular Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp., Or Gigaspora monosporum, Glomus spp., Laccaria spp. Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., Especially Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp., Streptomyces spp.

Beispiele für Pflanzenextrakte und solche Produkte, die von Mikroorganismen gebildet wurden inklusive Proteine und sekundäre Stoffwechselprodukte, die als biologische Schädlingsbekämpfungsmittel eingesetzt werden bzw. verwendet werden können, sind:
Allium sativum, Artemisia absinthium, Azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum, Chitin, Armour-Zen, Dryopteris filix-mas, Equisetum arvense,Fortune Aza, Fungastop, Heads Up (Chenopodium quinoa-Saponinextrakt), Pyrethrum/Pyrethrins, Quassia amara, Quercus, Quillaja, Regalia, "Requiem ™ Insecticide", Rotenon, Ryania/Ryanodine, Symphytum officinale, Tanacetum vulgare, Thymol, Triact 70, TriCon, Tropaeulum majus, Urtica dioica, Veratrin, Viscum album, Brassicacaeen-Extrakt, insbesondere Raps- oder Senfpulver.Examples of plant extracts and those products formed by microorganisms, including proteins and secondary metabolites, which can be used as biological pesticides are:
Allium sativum, Artemisia absinthium, Azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum, Chitin, Armor Zen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza, Fungastop, Heads Up (Chenopodium quinoa saponin extract), Pyrethrum / Pyrethrins, Quassia amara, Quercus, Quillaja, Regalia, Requiem ™ Insecticide, Rotenone, Ryania / Ryanodine, Symphytum officinale, Tanacetum vulgare, Thymol, Triact 70, TriCon, Tropaeulum majus, Urtica dioica, Veratrin, Viscum album, Brassicacaeen extract , in particular rapeseed or mustard powder.

Safener als MischpartnerSafener as mixing partner

Die Verbindungen der Formel (I) können mit Safenern kombiniert werden, wie zum Beispiel Benoxacor, Cloquintocet (-mexyl), Cyometrinil, Cyprosulfamide, Dichlormid, Fenchlorazole (-ethyl), Fenclorim, Flurazole, Fluxofenim, Furilazole, Isoxadifen (-ethyl), Mefenpyr (-diethyl), Naphthalic anhydride, Oxabetrinil, 2-Methoxy-N-({4-[(methylcarbamoyl)amino]phenyl}sulfonyl)benzamid ( CAS 129531-12-0 ), 4-(Dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane ( CAS 71526-07-3 ), 2,2,5-Trimethyl-3-(dichloroacetyl)-1,3-oxazolidine ( CAS 52836-31-4 ).The compounds of the formula (I) can be combined with safeners, for example Benoxacor, Cloquintocet (-mexyl), Cyometrinil, Cyprosulfamide, Dichlormid, Fenchlorazole (-ethyl), Fenclorim, Flurazole, Fluxofenim, Furilazole, Isoxadifen (-ethyl), Mefenpyr (-diethyl), naphthalic anhydride, oxabetrinil, 2-methoxy-N - ({4 - [(methylcarbamoyl) amino] phenyl} sulfonyl) benzamide ( CAS 129531-12-0 ), 4- (dichloroacetyl) -1-oxa-4-azaspiro [4.5] decane ( CAS 71526-07-3 ), 2,2,5-trimethyl-3- (dichloroacetyl) -1,3-oxazolidine ( CAS 52836-31-4 ).

Pflanzen und PflanzenteilePlants and plant parts

Erfindungsgemäß können alle Pflanzen und Pflanzenteile behandelt werden. Unter Pflanzen werden hierbei alle Pflanzen und Pflanzenpopulationen verstanden wie erwünschte und unerwünschte Wildpflanzen oder Kulturpflanzen (einschließlich natürlich vorkommender Kulturpflanzen), beispielsweise Getreide (Weizen, Reis, Triticale, Gerste, Roggen, Hafer), Mais, Soja, Kartoffel, Zuckerrüben, Zuckerrohr, Tomaten, Erbsen und andere Gemüsesorten, Baumwolle, Tabak, Raps, sowie Obstpflanzen (mit den Früchten Äpfel, Birnen, Zitrusfrüchten und Weintrauben). Kulturpflanzen können Pflanzen sein, die durch konventionelle Züchtungs- und Optimierungsmethoden oder durch biotechnologische und gentechnologische Methoden oder Kombinationen dieser Methoden erhalten werden können, einschließlich der transgenen Pflanzen und einschließlich der durch Sortenschutzrechte schützbaren oder nicht schützbaren Pflanzensorten. Unter Pflanzenteilen sollen alle oberirdischen und unterirdischen Teile und Organe der Pflanzen wie Spross, Blatt, Blüte und Wurzel verstanden werden, wobei beispielhaft Blätter, Nadeln, Stängel, Stämme, Blüten, Fruchtkörper, Früchte und Samen sowie Wurzeln, Knollen und Rhizome aufgeführt werden. Zu den Pflanzenteilen gehört auch Erntegut sowie vegetatives und generatives Vermehrungsmaterial, beispielsweise Stecklinge, Knollen, Rhizome, Ableger und Samen.According to the invention, all plants and parts of plants can be treated. Plants are understood to mean all plants and plant populations, such as desirable and unwanted wild plants or crops (including naturally occurring crops), for example cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugarcane, tomatoes , Peas and other vegetables, cotton, tobacco, oilseed rape, as well as fruit plants (with the fruits apples, pears, citrus fruits and grapes). Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or can not be protected by plant breeders' rights. Plant parts are understood to mean all aboveground and subterranean parts and organs of plants such as shoot, leaf, flower and root, examples of which include leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes. The plant parts also include crops and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, offshoots and seeds.

Die erfindungsgemäße Behandlung der Pflanzen und Pflanzenteile mit den Verbindungen der Formel (I) erfolgt direkt oder durch Einwirkung auf deren Umgebung, Lebensraum oder Lager-raum nach den üblichen Behandlungsmethoden, z.B. durch Tauchen, Sprühen, Ver¬dampfen, Ver¬nebeln, Streuen, Auf¬streichen, In¬jizieren und bei Ver¬mehrungs¬material, ins¬besondere bei Saatgut, weiterhin durch ein- oder mehr¬schichtiges Um¬hüllen.The treatment according to the invention of the plants and plant parts with the compounds of the formula (I) is carried out directly or by acting on their environment, habitat or storage room according to the usual treatment methods, e.g. by dipping, spraying, evaporating, fogging, spreading, brushing, injecting and in the case of propagation material, in particular in the case of seed, further by single-layer or multi-layer coating.

Wie bereits oben erwähnt können erfindungsgemäß alle Pflanzen und deren Teile behandelt werden. In einer bevorzugten Ausführungsform werden wild vorkommende oder durch konventionelle biologische Zuchtmethoden wie Kreuzung oder Protoplastenfusion erhaltene Pflanzenarten und Pflanzensorten sowie deren Teile behandelt. In einer weiteren bevorzugten Ausführungsform werden transgene Pflanzen und Pflanzensorten, die durch gentechnologische Methoden gegebenenfalls in Kombination mit konventionellen Methoden erhalten wurden (Genetically Modified Organisms) und deren Teile behandelt. Der Begriff "Teile" bzw. "Teile von Pflanzen" oder "Pflanzenteile" wurde oben erläutert. Besonders bevorzugt werden erfindungsgemäß Pflanzen der jeweils handelsüblichen oder in Gebrauch befindlichen Pflanzensorten behandelt. Unter Pflanzensorten versteht man Pflanzen mit neuen Eigenschaften ("Traits"), die sowohl durch konventionelle Züchtung, durch Mutagenese oder durch rekombinante DNA-Techniken gezüchtet worden sind. Dies können Sorten, Rassen, Bio- und Genotypen sein.As already mentioned above, all plants and their parts can be treated according to the invention. In a preferred embodiment, wild-type or plant species and plant varieties obtained by conventional biological breeding methods such as crossing or protoplast fusion and parts thereof are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated. The term "parts" or "parts of plants" or "plant parts" has been explained above. It is particularly preferred according to the invention to treat plants of the respective commercially available or in use plant cultivars. Plant varieties are understood as meaning plants having new traits which have been bred by conventional breeding, by mutagenesis or by recombinant DNA techniques. These may be varieties, breeds, biotypes and genotypes.

Transgene Pflanze, Saatgutbehandlung und IntegrationsereignisseTransgenic plant, seed treatment and integration events

Zu den bevorzugten erfindungsgemäß zu behandelnden transgenen (gen¬techno¬logisch erhaltenen) Pflanzen bzw. Pflanzensorten gehören alle Pflanzen, die durch die gen¬techno-logische Modifikation genetisches Material erhielten, welches diesen Pflanzen besondere vorteilhafte wertvolle Eigenschaften ("Traits") verleiht. Beispiele für solche Eigen¬schaften sind besseres Pflanzenwachstum, erhöhte Toleranz gegen¬über hohen oder niedrigen Temperaturen, erhöhte Toleranz gegen Trockenheit oder gegen Wasser- bzw. Bodensalzgehalt, erhöhte Blühleistung, erleichterte Ernte, Be¬schleunigung der Reife, höhere Ernteerträge, höhere Qualität und/oder höherer Er¬nährungs¬wert der Ernteprodukte, höhere Lagerfähigkeit und/oder Bearbeitbarkeit der Ernte¬produkte. Weitere und besonders hervorgehobene Beispiele für solche Eigen¬schaften sind eine erhöhte Abwehrfähigkeit der Pflanzen gegen tierische und mikrobielle Schäd¬linge, wie Insekten, Spinnentiere, Nematoden, Milben, Schnecken, bewirkt z.B. durch in den Pflanzen entstehende Toxine, insbesondere solche, die durch das genetische Material aus Bacillus Thuringiensis (z.B. durch die Gene CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb und CryIF sowie deren Kombinationen) in den Pflanzen erzeugt werden, ferner eine erhöhte Abwehrfähigkeit der Pflanzen gegen pflanzenpathogene Pilze, Bakterien und/oder Viren, bewirkt z.B. durch Systemisch Akquirierte Resistenz (SAR), Systemin, Phytoalexine, Elicitoren sowie Resistenzgene und entsprechend exprimierte Proteine und Toxine, sowie eine erhöhte Toleranz der Pflanzen gegen bestimmte herbizide Wirkstoffe, beispielsweise Imidazolinonen, Sulfonyl-harnstoffen, Glyphosate oder Phosphinotricin (z.B. "PAT"-Gen). Die jeweils die gewünschten Eigenschaften ("Traits") verleihenden Gene können auch in Kombinationen miteinander in den transgenen Pflanzen vorkommen. Als Beispiele transgener Pflanzen werden die wichtigen Kulturpflanzen, wie Getreide (Weizen, Reis, Triticale, Gerste, Roggen, Hafer), Mais, Soja, Kartoffel, Zuckerrüben, Zuckerrohr, Tomaten, Erbsen und andere Gemüsesorten, Baumwolle, Tabak, Raps, sowie Obstpflanzen (mit den Früchten Äpfel, Birnen, Zitrusfrüchten und Weintrauben) erwähnt, wobei Mais, Soja, Weizen, Reis, Kartoffel, Baumwolle, Zuckerrohr, Tabak und Raps besonders hervorgehoben werden. Als Eigenschaften ("Traits") werden besonders hervorgehoben die erhöhte Abwehrfähigkeit der Pflanzen gegen Insekten, Spinnentiere, Nematoden und Schnecken.The preferred plants or plant cultivars to be treated according to the invention which are to be treated include all plants which, as a result of the genetic modification, obtain genetic material which gives these plants particularly advantageous valuable properties ("traits"). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to water or soil salinity, increased flowering, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products. Further and particularly emphasized examples of such properties are an increased ability of the plants to defend themselves against animal and microbial pests, such as insects, arachnids, nematodes, mites, snails, causing e.g. by toxins produced in the plants, in particular those produced by the genetic material from Bacillus thuringiensis (eg by the genes CryIA (a), CryIA (b), CryIA (c), CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryIF as well as their combinations) are produced in the plants, furthermore an increased ability to repel the plants against phytopathogenic fungi, bacteria and / or viruses, eg Systemically acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins, and increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT" gene ). The genes which confer the desired properties ("traits") can also occur in combinations with one another in the transgenic plants. Examples of transgenic plants are the important crops such as cereals (wheat, rice, triticale, barley, rye, oats), corn, soy, potato, sugar beets, sugarcane, tomatoes, peas and other vegetables, cotton, tobacco, rape, and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with special emphasis on corn, soy, wheat, rice, potato, cotton, sugar cane, tobacco and oilseed rape. Traits that are particularly emphasized are the increased resistance of the plants to insects, arachnids, nematodes and snails.

Pflanzenschutz - BehandlungsartenPlant protection - types of treatment

Die Behandlung der Pflanzen und Pflanzenteile mit den Verbindungen der Formel (I) erfolgt direkt oder durch Einwirkung auf deren Umgebung, Lebensraum oder Lagerraum nach den üblichen Behandlungsmethoden, z.B. durch Tauchen, (Ver-) Spritzen, (Ver-)Sprühen, Berieseln, Verdampfen, Zerstäuben, Vernebeln, (Ver-)Streuen, Verschäumen, Bestreichen, Verstreichen, Injizieren, Gießen (drenchen), Tröpfchenbewässerung und bei Vermehrungsmaterial, insbesondere bei Saatgut, weiterhin durch Trockenbeizen, Nassbeizen, Schlämmbeizen, Inkrustieren, ein- oder mehrschichtiges Umhüllen, usw. Es ist ferner möglich, die Verbindungen der Formel (I) nach dem Ultra-Low-Volume-Verfahren auszubringen oder die Anwendungsform oder die Verbindung der Formel (I) selbst in den Boden zu injizieren.The treatment of the plants and plant parts with the compounds of formula (I) is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, for example by dipping, (spraying) spraying (spraying), sprinkling, evaporation , Spraying, misting, sprinkling, foaming, brushing, spreading, injecting, pouring, drip irrigation and, in the case of propagating material, in particular seed, further by dry pickling, wet pickling, slurry pickling, encrusting, single or multi-layer coating, etc It is also possible to use the compounds of the formula (I) according to the ultra-low-volume method or to inject the use form or compound of formula (I) itself into the soil.

Eine bevorzugte direkte Behandlung der Pflanzen ist die Blattapplikation, d.h. Verbindungen der Formel (I) werden auf das Blattwerk aufgebracht, wobei die Behandlungsfrequenz und die Aufwandmenge auf den Befallsdruck des jeweiligen Schädlings abgestimmt sein sollte.A preferred direct treatment of the plants is foliar application, i. Compounds of the formula (I) are applied to the foliage, wherein the treatment frequency and the application rate should be matched to the infestation pressure of the respective pest.

Bei systemisch wirksamen Verbindungen gelangen die Verbindungen der Formel (I) auch über das Wurzelwerk in die Pflanzen. Die Behandlung der Pflanzen erfolgt dann durch Einwirkung der Verbindungen der Formel (I) auf den Lebensraum der Pflanze. Das kann beispielsweise durch Drenchen, Einmischen in den Boden oder die Nährlösung sein, d.h. der Standort der Pflanze (z.B. Boden oder hydroponische Systeme) wird mit einer flüssigen Form der Verbindungen der Formel (I) getränkt, oder durch die Bodenapplikation, d.h. die Verbindungen der Formel (I) werden in fester Form, (z.B. in Form eines Granulats) in den Standort der Pflanzen eingebracht. Bei Wasserreiskulturen kann das auch durch Zudosieren der Verbindung der Formel (I) in einer festen Anwendungsform (z.B. als Granulat) in ein überflutetes Reisfeld sein.In the case of systemically active compounds, the compounds of the formula (I) also enter the plants via the root system. The treatment of the plants is then carried out by the action of the compounds of formula (I) on the habitat of the plant. This may be, for example, by drenching, mixing into the soil or the nutrient solution, i. the location of the plant (e.g., soil or hydroponic systems) is soaked in a liquid form of the compounds of formula (I), or by the soil application, i. the compounds of formula (I) are incorporated in solid form (e.g., in the form of granules) at the plant site. In water rice crops, this may also be by metered addition of the compound of formula (I) in a solid form (e.g., as granules) into a flooded paddy field.

Saatgutbehandlungseed treatment

Die Bekämpfung von tierischen Schädlingen durch die Behandlung des Saatguts von Pflanzen ist seit langem bekannt und ist Gegenstand ständiger Verbesserungen. Dennoch ergeben sich bei der Behandlung von Saatgut eine Reihe von Problemen, die nicht immer zufriedenstellend gelöst werden können. So ist es erstrebenswert, Verfahren zum Schutz des Saatguts und der keimenden Pflanze zu entwickeln, die das zusätzliche Ausbringen von Schädlingsbekämpfungsmitteln bei der Lagerung, nach der Saat oder nach dem Auflaufen der Pflanzen überflüssig machen oder zumindest deutlich verringern. Es ist weiterhin erstrebenswert, die Menge des eingesetzten Wirkstoffs dahingehend zu optimieren, dass das Saatgut und die keimende Pflanze vor dem Befall durch tierische Schädlinge bestmöglich geschützt werden, ohne jedoch die Pflanze selbst durch den eingesetzten Wirkstoff zu schädigen. Insbesondere sollten Verfahren zur Behandlung von Saatgut auch die intrinsischen insektiziden bzw. nematiziden Eigenschaften schädlingsresistenter bzw. - toleranter transgener Pflanzen einbeziehen, um einen optimalen Schutz des Saatguts und der keimenden Pflanze bei einem minimalen Aufwand an Schädlingsbekämpfungsmitteln zu erreichen.The control of animal pests by the treatment of the seed of plants has long been known and is the subject of constant improvement. Nevertheless, there are a number of problems in the treatment of seeds that can not always be satisfactorily resolved. Thus, it is desirable to develop methods for protecting the seed and the germinating plant which eliminate or at least significantly reduce the additional application of pesticides during storage, after sowing or after emergence of the plants. It is also desirable to optimize the amount of the active ingredient used in such a way that the seed and the germinating plant are best protected against attack by animal pests, but without damaging the plant itself by the active ingredient used. In particular, seed treatment methods should also incorporate the intrinsic insecticidal or nematicidal properties of pest-resistant transgenic plants in order to achieve optimum protection of the seed and germinating plant with a minimum of pesticide cost.

Die vorliegende Erfindung bezieht sich daher insbesondere auch auf ein Verfahren zum Schutz von Saatgut und keimenden Pflanzen vor dem Befall von Schädlingen, indem das Saatgut mit einer der Verbindungen der Formel (I) behandelt wird. Das erfindungsgemäße Verfahren zum Schutz von Saatgut und keimenden Pflanzen vor dem Befall von Schädlingen umfasst ferner ein Verfahren, in dem das Saatgut gleichzeitig in einem Vorgang oder sequentiell mit einer Verbindung der Formel (I) und Mischungspartner behandelt wird. Es umfasst ferner auch ein Verfahren, in dem das Saatgut zu unterschiedlichen Zeiten mit einer Verbindung der Formel (I) und Mischungspartner behandelt wird.The present invention therefore more particularly relates to a method of protecting seed and germinating plants from attack by pests by treating the seed with one of the compounds of formula (I). The method according to the invention for the protection of seeds and germinating plants from infestation by pests further comprises a method in which the seed is treated simultaneously in one operation or sequentially with a compound of formula (I) and mixing partner. It also also includes a method in which the seed is treated at different times with a compound of formula (I) and mixing partner.

Die Erfindung bezieht sich ebenfalls auf die Verwendung der Verbindungen der Formel (I) zur Behandlung von Saatgut zum Schutz des Saatguts und der daraus entstehenden Pflanze vor tierischen Schädlingen.The invention also relates to the use of the compounds of the formula (I) for the treatment of seed for the protection of the seed and the resulting plant from animal pests.

Weiterhin bezieht sich die Erfindung auf Saatgut, welches zum Schutz vor tierischen Schädlingen mit einer Verbindung der Formel (I) behandelt wurde. Die Erfindung bezieht sich auch auf Saatgut, welches zur gleichen Zeit mit einer Verbindung der Formel (I) und Mischungspartner behandelt wurde. Die Erfindung bezieht sich weiterhin auf Saatgut, welches zu unterschiedlichen Zeiten mit einer Verbindung der Formel (I) und Mischungspartner behandelt wurde. Bei Saatgut, welches zu unterschiedlichen Zeiten mit einer Verbindung der Formel (I) und Mischungspartner behandelt wurde, können die einzelnen Substanzen in unterschiedlichen Schichten auf dem Saatgut enthalten sein. Dabei können die Schichten, die eine Verbindung der Formel (I) und Mischungspartner enthalten, gegebenenfalls durch eine Zwischenschicht getrennt sein. Die Erfindung bezieht sich auch auf Saatgut, bei dem eine Verbindung der Formel (I) und Mischungspartner als Bestandteil einer Umhüllung oder als weitere Schicht oder weitere Schichten zusätzlich zu einer Umhüllung aufgebracht sind.Furthermore, the invention relates to seed which has been treated for protection against animal pests with a compound of formula (I). The invention also relates to seed treated at the same time with a compound of formula (I) and mixing partner. The invention further relates to seed which has been treated at different times with a compound of formula (I) and mixing partner. In the case of seed which has been treated at different times with a compound of formula (I) and mixing partner, the individual substances may be contained in different layers on the seed. In this case, the layers which comprise a compound of the formula (I) and mixture partners may optionally be separated by an intermediate layer. The invention also relates to seed in which a compound of the formula (I) and mixing partner are applied as a constituent of a coating or as a further layer or further layers in addition to a coating.

Des Weiteren bezieht sich die Erfindung auf Saatgut, welches nach der Behandlung mit einer Verbindung der Formel (I) einem Filmcoating - Verfahren unterzogen wird, um Staubabrieb am Saatgut zu vermeiden.Furthermore, the invention relates to seed which, after treatment with a compound of the formula (I), is subjected to a film coating process in order to avoid dust abrasion on the seed.

Einer der auftretenden Vorteile, wenn eine der Verbindungen der Formel (I) systemisch wirkt, ist es, dass die Behandlung des Saatguts nicht nur das Saatgut selbst, sondern auch die daraus hervorgehenden Pflanzen nach dem Auflaufen vor tierischen Schädlingen schützt. Auf diese Weise kann die unmittelbare Behandlung der Kultur zum Zeitpunkt der Aussaat oder kurz danach entfallen.One of the advantages that occurs when one of the compounds of the formula (I) acts systemically is that the treatment of the seed protects not only the seed itself, but also the resulting plants after emergence from animal pests. In this way, the immediate treatment of the culture at the time of sowing or shortly afterwards can be omitted.

Ein weiterer Vorteil ist darin zu sehen, dass durch die Behandlung des Saatguts mit einer Verbindung der Formel (I) Keimung und Auflauf des behandelten Saatguts gefördert werden können.Another advantage is the fact that by treating the seed with a compound of formula (I) germination and emergence of the treated seed can be promoted.

Ebenso ist es als vorteilhaft anzusehen, dass Verbindungen der Formel (I) insbesondere auch bei transgenem Saatgut eingesetzt werden können.Likewise, it is considered to be advantageous that compounds of the formula (I) can also be used in particular in the case of transgenic seed.

Verbindungen der Formel (I) können ferner in Kombination mit Mitteln der Signaltechnologie eingesetzt werden, wodurch eine bessere Besiedlung mit Symbionten, wie zum Beispiel Rhizobien, Mycorrhiza und/oder endophytischen Bakterien oder Pilzen, stattfindet und/oder es zu einer optimierten Stickstofffixierung kommt.Compounds of formula (I) may also be used in combination with signal technology agents whereby better colonization with symbionts such as rhizobia, mycorrhiza and / or endophytic bacteria or fungi takes place and / or optimized nitrogen fixation occurs.

Die Verbindungen der Formel (I) eignen sich zum Schutz von Saatgut jeglicher Pflanzensorte, die in der Landwirtschaft, im Gewächshaus, in Forsten oder im Gartenbau eingesetzt wird. Insbesondere handelt es sich dabei um Saatgut von Getreide (z. B. Weizen, Gerste, Roggen, Hirse und Hafer), Mais, Baum-wolle, Soja, Reis, Kartoffeln, Sonnenblume, Kaffee, Tabak, Canola, Raps, Rübe (z.B. Zuckerrübe und Futterrübe), Erdnuss, Gemüse (z. B. Tomate, Gurke, Bohne, Kohlgewächse, Zwiebeln und Salat), Obstpflanzen, Rasen und Zierpflanzen. Besondere Bedeutung kommt der Behandlung des Saatguts von Getreide (wie Weizen, Gerste, Roggen und Hafer), Mais, Soja, Baumwolle, Canola, Raps und Reis zu.The compounds of the formula (I) are suitable for the protection of seed of any plant variety used in agriculture, in the greenhouse, in forests or in horticulture. In particular, these are seeds of cereals (eg wheat, barley, rye, millet and oats), corn, cotton, soy, rice, potatoes, sunflower, coffee, tobacco, canola, rape, turnip (eg sugar beet and fodder beet), peanut, vegetables (eg tomato, cucumber, bean, cabbage, onions and lettuce), fruit plants, turf and ornamental plants. Of particular importance is the treatment of seeds of cereals (such as wheat, barley, rye and oats), corn, soya, cotton, canola, oilseed rape and rice.

Wie vorstehend bereits erwähnt, kommt auch der Behandlung von transgenem Saatgut mit einer Verbindung der Formel (I) eine besondere Bedeutung zu. Dabei handelt es sich um das Saatgut von Pflanzen, die in der Regel zumindest ein heterologes Gen enthalten, das die Expression eines Polypeptids mit insbesondere insektiziden bzw. nematiziden Eigenschaften steuert. Die heterologen Gene in transgenem Saatgut können dabei aus Mikro-organismen wie Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus oder Gliocladium stammen. Die vorliegende Erfindung eignet sich besonders für die Behandlung von trans-genem Saatgut, das zumindest ein heterologes Gen enthält, das aus Bacillus sp. stammt. Besonders bevorzugt handelt es sich dabei um ein heterologes Gen, das aus Bacillus thuringiensis stammt.As already mentioned above, the treatment of transgenic seed with a compound of the formula (I) is also of particular importance. These are the seeds of plants, which as a rule contain at least one heterologous gene which controls the expression of a polypeptide having in particular insecticidal or nematicidal properties. The heterologous genes in transgenic seed can be derived from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. The present invention is particularly useful for the treatment of transgenic seed containing at least one heterologous gene derived from Bacillus sp. comes. Most preferably, this is a heterologous gene derived from Bacillus thuringiensis.

Im Rahmen der vorliegenden Erfindung wird die Verbindung der Formel (I) auf das Saatgut aufgebracht. Vorzugsweise wird das Saatgut in einem Zustand behandelt, in dem es so stabil ist, dass keine Schäden bei der Behandlung auftreten. Im Allgemeinen kann die Behandlung des Saatguts zu jedem Zeitpunkt zwischen der Ernte und der Aussaat erfolgen. Üblicherweise wird Saatgut verwendet, das von der Pflanze getrennt und von Kolben, Schalen, Stängeln, Hülle, Wolle oder Fruchtfleisch befreit wurde. So kann zum Beispiel Saatgut verwendet werden, das geerntet, gereinigt und bis zu einem lagerfähigen Feuchtigkeitsgehalt getrocknet wurde. Alternativ kann auch Saatgut verwendet werden, das nach dem Trocknen z.B. mit Wasser behandelt und dann erneut getrocknet wurde, zum Beispiel Priming. Im Falle von Reissaatgut ist es auch möglich Saatgut zu verwenden, das zum Beispiel in Wasser bis zu einem bestimmten Stadium vorgequollen wurde (pigeon breast Stadium), was zu einer verbesserten Keimung und zu einem gleichmäßigeren Auflaufen führt.In the context of the present invention, the compound of the formula (I) is applied to the seed. Preferably, the seed is treated in a state where it is so stable that no damage occurs during the treatment. In general, the treatment of the seed can be done at any time between harvesting and sowing. Usually, seed is used which has been separated from the plant and freed from flasks, shells, stems, hull, wool or pulp. For example, seed may be used that has been harvested, cleaned and dried to a moisture content that is storable. Alternatively, seed may also be used which, after drying, e.g. treated with water and then dried again, for example priming. In the case of rice seed, it is also possible to use seeds that have been pre-swollen in water, for example, to a certain stage (pigeon breast stage), resulting in improved germination and more even emergence.

Im Allgemeinen muss bei der Behandlung des Saatguts darauf geachtet werden, dass die Menge der auf das Saatgut aufgebrachten Verbindung der Formel (I) und/oder weiterer Zusatzstoffe so gewählt wird, dass die Keimung des Saatguts nicht beeinträchtigt bzw. die daraus hervorgehende Pflanze nicht geschädigt wird. Dies ist vor allem bei Wirkstoffen zu beachten, die in bestimmten Aufwandmengen phytotoxische Effekte zeigen können.In general, when treating seed, care must be taken to ensure that the amount of compound of formula (I) and / or other additives applied to the seed is not such as to affect the germination of the seed or to damage the resulting plant becomes. This is especially important for active ingredients, which can show phytotoxic effects in certain application rates.

Die Verbindungen der Formel (I) werden in der Regel in Form einer geeigneten Formulierung auf das Saatgut aufgebracht. Geeignete Formulierungen und Verfahren für die Saatgutbehandlung sind dem Fachmann bekannt.The compounds of the formula (I) are generally applied to the seed in the form of a suitable formulation. Suitable formulations and methods for seed treatment are known to those skilled in the art.

Die Verbindungen der Formel (I) können in die üblichen Beizmittel-Formulierungen überführt werden, wie Lösungen, Emulsionen, Suspensionen, Pulver, Schäume, Slurries oder andere Hüllmassen für Saatgut, sowie ULV-Formulierungen.The compounds of the formula (I) can be converted into the customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other seed coating compositions, and also ULV formulations.

Diese Formulierungen werden in bekannter Weise hergestellt, indem man Verbindungen der Formel (I) mit üblichen Zusatzstoffen vermischt, wie zum Beispiel übliche Streckmittel sowie Lösungs- oder Verdünnungsmittel, Farbstoffe, Netzmittel, Dispergiermittel, Emulgatoren, Entschäumer, Konservierungsmittel, sekundäre Verdickungsmittel, Kleber, Gibberelline und auch Wasser.These formulations are prepared in a known manner by mixing compounds of formula (I) with conventional additives, such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and also water.

Als Farbstoffe, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen alle für derartige Zwecke üblichen Farbstoffe in Betracht. Dabei sind sowohl in Wasser wenig lösliche Pigmente als auch in Wasser lösliche Farbstoffe verwendbar. Als Beispiele genannt seien die unter den Bezeichnungen Rhodamin B, C.I. Pigment Red 112 und C.I. Solvent Red 1 bekannten Farbstoffe.Dyes which may be present in the seed dressing formulations which can be used according to the invention are all dyes customary for such purposes. Both water-insoluble pigments and water-soluble dyes are useful in this case. Examples which may be mentioned under the names rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red 1 known dyes.

Als Netzmittel, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen alle zur Formulierung von agrochemischen Wirkstoffen üblichen, die Benetzung fördernden Stoffe in Frage. Vorzugsweise verwendbar sind Alkylnaphthalin-Sulfonate, wie Diisopropyl- oder Diisobutyl-naphthalin-Sulfonate.Suitable wetting agents which may be present in the seed dressing formulations which can be used according to the invention are all wetting-promoting substances customary for the formulation of agrochemical active compounds. Preferably used are alkylnaphthalene sulfonates, such as diisopropyl or diisobutyl naphthalene sulfonates.

Als Dispergiermittel und/oder Emulgatoren, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen alle zur Formulierung von agrochemischen Wirkstoffen üblichen nichtionischen, anionischen und kationischen Dispergiermittel in Betracht. Vor-zugsweise verwendbar sind nichtionische oder anionische Dispergiermittel oder Gemische von nichtionischen oder anionischen Dispergiermitteln. Als geeignete nichtionische Dispergiermittel sind insbesondere Ethylenoxid-Propylenoxid Blockpolymere, Alkylphenolpolyglykolether sowie Tristryrylphenolpolyglykolether und deren phosphatierte oder sulfatierte Derivate zu nennen. Geeignete anionische Dispergiermittel sind insbesondere Ligninsulfonate, Polyacrylsäuresalze und Arylsulfonat-Formaldehydkondensate.Suitable dispersants and / or emulsifiers which may be present in the seed dressing formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active compounds. Preference is given to using nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants. Particularly suitable nonionic dispersants are, in particular, ethylene oxide-propylene oxide, block polymers, alkylphenol polyglycol ethers and tristryrylphenol polyglycol ethers and their phosphated or sulfated derivatives. Suitable anionic dispersants are in particular lignosulfonates, polyacrylic acid salts and arylsulfonate-formaldehyde condensates.

Als Entschäumer können in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen alle zur Formulierung von agrochemischen Wirkstoffen üblichen schaumhemmenden Stoffe enthalten sein. Vorzugsweise verwendbar sind Silikonentschäumer und Magnesiumstearat.Defoamers which may be present in the seed-dressing formulations which can be used according to the invention are all foam-inhibiting substances customary for the formulation of agrochemical active compounds. Preferably usable are silicone defoamers and magnesium stearate.

Als Konservierungsmittel können in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen alle für derartige Zwecke in agrochemischen Mitteln einsetzbaren Stoffe vorhanden sein. Beispielhaft genannt seien Dichlorophen und Benzylalkoholhemiformal.Preservatives which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Examples include dichlorophen and Benzylalkoholhemiformal.

Als sekundäre Verdickungsmittel, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen alle für derartige Zwecke in agrochemischen Mitteln einsetzbaren Stoffe in Frage. Vorzugsweise in Betracht kommen Cellulosederivate, Acrylsäurederivate, Xanthan, modifizierte Tone und hochdisperse Kieselsäure.Suitable secondary thickeners which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Preference is given to cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.

Als Kleber, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen alle üblichen in Beizmitteln einsetzbaren Bindemittel in Frage. Vorzugsweise genannt seien Polyvinylpyrrolidon, Polyvinylacetat, Polyvinylalkohol und Tylose.Suitable adhesives which may be present in the seed dressing formulations which can be used according to the invention are all customary binders which can be used in pickling agents. Preferably mentioned are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose.

Als Gibberelline, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen vorzugsweise die Gibberelline A1, A3 (= Gibberellinsäure), A4 und A7 infrage, besonders bevorzugt verwendet man die Gibberellinsäure. Die Gibberelline sind bekannt (vgl. R. Wegler "Chemie der Pflanzenschutz- und Schädlingsbekämpfungsmittel", Bd. 2, Springer Verlag, 1970, S. 401-412 ).Gibberellins which may be present in the seed dressing formulations which can be used according to the invention are preferably the gibberellins A1, A3 (= gibberellic acid), A4 and A7, with particular preference gibberellic acid. The gibberellins are known (cf. R. Wegler "Chemie der Pflanzenschutz- und Schädlingsbekungsmittel", Vol. 2, Springer Verlag, 1970, p. 401-412 ).

Die erfindungsgemäß verwendbaren Beizmittel-Formulierungen können entweder direkt oder nach vorherigem Verdünnen mit Wasser zur Behandlung von Saatgut der verschiedensten Art eingesetzt werden. So lassen sich die Konzentrate oder die daraus durch Verdünnen mit Wasser erhältlichen Zubereitungen einsetzen zur Beizung des Saatgutes von Getreide, wie Weizen, Gerste, Roggen, Hafer und Triticale, sowie des Saatgutes von Mais, Reis, Raps, Erbsen, Bohnen, Baumwolle, Sonnenblumen, Soja und Rüben oder auch von Gemüsesaatgut der verschiedensten Natur. Die erfindungsgemäß verwendbaren Beizmittel-Formulierungen oder deren verdünnte Anwendungsformen können auch zum Beizen von Saatgut transgener Pflanzen eingesetzt werden.The seed dressing formulations which can be used according to the invention can be used either directly or after prior dilution with water for the treatment of seed of various kinds. Thus, the concentrates or the preparations obtainable therefrom by dilution with water can be used for dressing the seeds of cereals such as wheat, barley, rye, oats and triticale, as well as the seeds of corn, rice, rape, peas, beans, cotton, sunflowers , Soy and beets or vegetable seed of various nature. The seed dressing formulations which can be used according to the invention or their dilute application forms can also be used for pickling seeds of transgenic plants.

Zur Behandlung von Saatgut mit den erfindungsgemäß verwendbaren Beizmittel-Formulierungen oder daraus hergestellten Anwendungsformen kommen alle üblicherweise für die Beizung einsetzbaren Mischgeräte in Betracht. Im einzelnen geht man bei der Beizung so vor, dass man das Saatgut in einen Mischer im diskontinuierlichem oder kontinuierlichem Betrieb gibt, die jeweils gewünschte Menge an Beizmittel-Formulierungen entweder als solche oder nach vorherigem Verdünnen mit Wasser hinzufügt und bis zur gleichmäßigen Verteilung der Formulierung auf dem Saatgut mischt. Gegebenenfalls schließt sich ein Trocknungsvorgang an.For the treatment of seed with the seed dressing formulations which can be used according to the invention or the use forms prepared therefrom, all mixing devices which can usually be used for the dressing can be considered. Specifically, the pickling is done by placing the seed in a batch or continuous mixer, adding either desired amount of seed dressing formulations, either as such or after prior dilution with water, and until the formulation is evenly distributed mix the seed. Optionally, a drying process follows.

Die Aufwandmenge an den erfindungsgemäß verwendbaren Beizmittel-Formulierungen kann inner-halb eines größeren Bereiches variiert werden. Sie richtet sich nach dem jeweiligen Gehalt der Verbindungen der Formel (I) in den Formulierungen und nach dem Saatgut. Die Aufwandmengen bei der Verbindung der Formel (I) liegen im Allgemeinen zwischen 0,001 und 50 g pro Kilogramm Saatgut, vorzugsweise zwischen 0,01 und 15 g pro Kilogramm Saatgut.The application rate of the seed dressing formulations which can be used according to the invention can be varied within a relatively wide range. It depends on the particular content of the compounds of the formula (I) in the formulations and on the seed. The application rates for the compound of the formula (I) are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 15 g per kilogram of seed.

Tiergesundheitanimal Health

Auf dem Gebiet der Tiergesundheit, d.h. dem Gebiet der Tiermedizin, sind die Verbindungen der Formel (I) gegen Tierparasiten, insbesondere Ektoparasiten oder Endoparasiten, wirksam. Der Begriff Endoparasiten umfasst insbesondere Helminthen und Protozoa wie Kokzidien. Ektoparasiten sind typischerweise und bevorzugt Arthropoden, insbesondere Insekten und Akariden.In the field of animal health, ie the veterinary field, the compounds of formula (I) are active against animal parasites, in particular ectoparasites or endoparasites. The term endoparasite includes in particular helminths and protozoa such as coccidia. Ectoparasites are typically and preferably arthropods, especially insects and acarids.

Auf dem Gebiet der Tiermedizin eignen sich die Verbindungen der Formel (I), die eine günstige Toxizität gegenüber Warmblütern aufweisen, für die Bekämpfung von Parasiten, die in der Tierzucht und Tierhaltung bei Nutztieren, Zuchttieren, Zootieren, Laboratoriumstieren, Versuchstieren und Haustieren auftreten. Sie sind gegen alle oder einzelne Entwicklungsstadien der Parasiten wirksam.In the veterinary field, the compounds of formula (I) which are of low toxicity to warm-blooded animals are useful in the control of parasites found in livestock and livestock in livestock, breeding animals, zoo animals, laboratory animals, experimental animals and domestic animals. They are effective against all or individual stages of parasite development.

Zu den landwirtschaftlichen Nutztieren zählen zum Beispiel Säugetiere wie Schafe, Ziegen, Pferde, Esel, Kamele, Büffel, Kaninchen, Rentiere, Damhirsche und insbesondere Rinder und Schweine; Geflügel wie Truthähne, Enten, Gänse und insbesondere Hühner; Fische und Krustentiere, z.B. in der Aquakultur und auch Insekten wie Bienen.Farm animals include, for example, mammals such as sheep, goats, horses, donkeys, camels, buffaloes, rabbits, reindeer, fallow deer, and especially cattle and pigs; Poultry such as turkeys, ducks, geese and, in particular, chickens; Fish and shellfish, e.g. in aquaculture and also insects like bees.

Zu den Haustieren zählen zum Beispiel Säugetiere wie Hamster, Meerschweinchen, Ratten, Mäuse, Chinchillas, Frettchen und insbesondere Hunde, Katzen, Stubenvögel, Reptilien, Amphibien und Aquariumfische.The domestic animals include, for example, mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets, and especially dogs, cats, caged birds, reptiles, amphibians and aquarium fish.

Gemäß einer bevorzugten Ausführungsform werden die Verbindungen der Formel (I) an Säugetiere verabreicht.In a preferred embodiment, the compounds of formula (I) are administered to mammals.

Gemäß einer weiteren bevorzugten Ausführungsform werden die Verbindungen der Formel (I) an Vögel, nämlich Stubenvögel und insbesondere Geflügel, verabreicht.According to a further preferred embodiment, the compounds of the formula (I) are administered to birds, namely caged birds and in particular poultry.

Durch Verwendung der Verbindungen der Formel (I) für die Bekämpfung von Tierparasiten sollen Krankheit, Todesfälle und Leistungsminderungen (bei Fleisch, Milch, Wolle, Häuten, Eiern, Honig und dergleichen) verringert bzw. vorgebeugt werden, so dass eine wirtschaftlichere und einfachere Tierhaltung ermöglicht wird und ein besseres Wohlbefinden der Tiere erzielbar ist.By using the compounds of formula (I) for the control of animal parasites disease, deaths and reductions in performance (in meat, milk, wool, hides, eggs, honey and the like) should be reduced or prevented, so that a more economical and easier animal husbandry allows and a better well-being of the animals is achievable.

In Bezug auf das Gebiet der Tiergesundheit bedeutet der Begriff "Bekämpfung" oder "bekämpfen", dass durch die Verbindungen der Formel (I) wirksam das Auftreten des jeweiligen Parasiten in einem Tier, das mit solchen Parasiten in einem harmlosen Ausmaß infiziert ist, reduziert werden kann. Genauer gesagt bedeutet "bekämpfen" im vorliegenden Zusammenhang, dass die Verbindung der Formel (I) den jeweiligen Parasiten abtöten, sein Wachstum verhindern oder seine Vermehrung verhindern kann.With regard to the field of animal health, the term "control" or "combat" means that the compounds of formula (I) effectively reduce the incidence of the particular parasite in an animal infected with such parasites to a harmless extent can. More specifically, "combating" in the present context means that the compound of formula (I) can kill the respective parasite, prevent its growth or prevent its replication.

Zu den Arthropoden zählen:

  • aus der Ordnung Anoplurida, zum Beispiel Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.; aus der Ordnung Mallophagida und den Unterordnungen Amblycerina and Ischnocerina, zum Beispiel Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.; aus der Ordnung Diptera und den Unterordnungen Nematocerina und Brachycerina, zum Beispiel Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Odagmia spp., Wilhelmia spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp., Rhinoestrus spp., Tipula spp.; aus der Ordnung Siphonapterida, zum Beispiel Pulex spp., Ctenocephalides spp., Tunga spp., Xenopsylla spp., Ceratophyllus spp.;
  • aus der Ordnung Heteropterida, zum Beispiel Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.; sowie Lästlinge und Hygieneschädlinge aus der Ordnung Blattarida.
The arthropods include:
  • from the order Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp .; from the order Mallophagida and the suborders Amblycerina and Ischnocerina, for example Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp .; from the order Diptera and the suborders Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Odagmia Spp., Wilhelmia spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp. Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp , Lipoptena spp., Melophagus spp., Rhinoestrus spp., Tipula spp .; from the order Siphonapterida, for example Pulex spp., Ctenocephalides spp., Tunga spp., Xenopsylla spp., Ceratophyllus spp .;
  • from the order Heteropterida, for example Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp .; as well as pests and hygiene pests from the order Blattarida.

Weiterhin zählen zu den Arthropoden:Furthermore, the arthropods include:

Aus der Unterklasse Akari (Acarina) und der Ordnung Metastigmata, zum Beispiel aus der Familie Argasidae, wie Argas spp., Ornithodorus spp., Otobius spp., aus der Familie Ixodidae, wie Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp. Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp. (die ursprüngliche Gattung der mehrwirtigen Zecken); aus der Ordnung Mesostigmata, wie Dermanyssus spp., Omithonyssus spp., Pneumonyssus spp., Raillietia spp., Pneumonyssus spp., Stemostoma spp., Varroa spp., Acarapis spp.; aus der Ordnung Actinedida (Prostigmata), zum Beispiel Acarapis spp., Cheyletiella spp., Omithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Neotrombiculla spp., Listrophorus spp.; und aus der Ordnung Acaridida (Astigmata), zum Beispiel Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp..From the subclass Akari (Acarina) and the order Metastigmata, for example from the family Argasidae, such as Argas spp., Ornithodorus spp., Otobius spp., From the family Ixodidae, such as Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp. Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp. (the original genus of multi-pronged ticks); from the order Mesostigmata, such as Dermanyssus spp., Omithonyssus spp., Pneumonyssus spp., Raillietia spp., Pneumonyssus spp., Stemostoma spp., Varroa spp., Acarapis spp .; from the order Actinedida (Prostigmata), for example Acarapis spp., Cheyletiella spp., Omithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Neotrombiculla spp., Listrophorus spp .; and from the order Acaridida (Astigmata), for example Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp. , Knemidocoptes spp., Cytodites spp., Laminosioptes spp.

Zu parasitären Protozoen zählen:Parasitic protozoa include:

Mastigophora (Flagellata), wie zum Beispiel Trypanosomatidae, zum Beispiel Trypanosoma b. brucei, T.b. gambiense, T.b. rhodesiense, T. congolense, T. cruzi, T. evansi, T. equinum, T. lewisi, T. percae, T. simiae, T. vivax, Leishmania brasiliensis, L. donovani, L. tropica, wie zum Beispiel Trichomonadidae, zum Beispiel Giardia lamblia, G. canis;
Sarcomastigophora (Rhizopoda), wie Entamoebidae, zum Beispiel Entamoeba histolytica, Hartmanellidae, zum Beispiel Acanthamoeba sp., Harmanella sp.;
Apicomplexa (Sporozoa), wie Eimeridae, zum Beispiel Eimeria acervulina, E. adenoides, E. alabamensis, E. anatis, E. anserina, E. arloingi, E. ashata, E. aubumensis, E. bovis, E. brunetti, E. canis, E. chinchillae, E. clupearum, E. columbae, E. contorta, E. crandalis, E. debliecki, E. dispersa, E. ellipsoidales, E. falciformis, E. faurei, E. flavescens, E. gallopavonis, E. hagani, E. intestinalis, E. iroquoina, E. irresidua, E. labbeana, E. leucarti, E. magna, E. maxima, E. media, E. meleagridis, E. meleagrimitis, E. mitis, E. necatrix, E. ninakohlyakimovae, E. ovis, E. parva, E. pavonis, E. perforans, E. phasani, E. piriformis, E. praecox, E. residua, E. scabra, E. spec., E. stiedai, E. suis, E. tenella, E. truncata, E. truttae, E. zuernii, Globidium spec., Isospora belli, I. canis, I. felis, I. ohioensis, I. rivolta, I. spec., I. suis, Cystisospora spec., Cryptosporidium spec., insbesondere C. parvum; wie Toxoplasmadidae, zum Beispiel Toxoplasma gondii, Hammondia heydornii, Neospora caninum, Besnoitia besnoitii; wie Sarcocystidae, zum Beispiel Sarcocystis bovicanis, S. bovihominis, S. ovicanis, S. ovifelis, S. neurona, S. spec., S. suihominis, wie Leucozoidae, zum Beispiel Leucozytozoon simondi, wie Plasmodiidae, zum Beispiel Plasmodium berghei, P. falciparum, P. malariae, P. ovale, P. vivax, P. spec., wie Piroplasmea, zum Beispiel Babesia argentina, B. bovis, B. canis, B. spec., Theileria parva, Theileria spec., wie Adeleina, zum Beispiel Hepatozoon canis, H. spec..Mastigophora (Flagellata), such as Trypanosomatidae, for example Trypanosoma b. brucei, Tb gambiense, Tb rhodesiense, T. congolense, T. cruzi, T. evansi, T. equinum, T. lewisi, T. percae, T. simiae, T. vivax, Leishmania brasiliensis, L. donovani, L. tropica such as Trichomonadidae, for example Giardia lamblia, G. canis;
Sarcomastigophora (Rhizopoda) such as Entamoebidae, for example Entamoeba histolytica, Hartmanellidae, for example Acanthamoeba sp., Harmanella sp .;
Apicomplexa (Sporozoa), such as Eimeridae, for example Eimeria acervulina, E. adenoides, E. alabamensis, E. anatis, E. anserina, E. arloingi, E. ashata, E. aubumensis, E. bovis, E. brunetti, E canis, E. chinchillae, E. clupearum, E. columbae, E. contorta, E. crandalis, E. debliecki, E. dispersa, E. ellipsoidales, E. falciformis, E. faurei, E. flavescens, E. gallopavonis , E. hagani, E. intestinalis, E. iroquoina, E. irresidua, E. labbeana, E. leucarti, E. magna, E. maxima, E.media, E. meleagridis, E. meleagrimitis, E. mitis, E necatrix, E. ninakohlyakimovae, E.ovis, E.parva, E.pavonis, E. perforans, E. phasani, E. piriformis, E. praecox, E. residua, E. scabra, E. spec., E. stiedai, E. suis, E. tenella, E. truncata, E. truttae, E. zuernii, Globidium spec., Isospora belli, I. canis, I. felis, I. ohioensis, I. rivolta, I. spec., I. suis, Cystisospora spec., Cryptosporidium spec., in particular C. parvum; such as Toxoplasmadidae, for example Toxoplasma gondii, Hammondia heydornii, Neospora caninum, Besnoitia besnoitii; such as Sarcocystidae, for example Sarcocystis bovicanis, S. bovihominis, S. ovicanis, S. ovifelis, S. neurona, S. spec., S. suihominis, such as Leucozoidae, for example Leucocytozoon simondi, such as Plasmodiidae, for example Plasmodium berghei, P falciparum, P. malariae, P. ovale, P. vivax, P. spec., such as piroplasmea, for example Babesia argentina, B. bovis, B. canis, B. spec., Theileria parva, Theileria spec., as Adeleina , for example Hepatozoon canis, H. spec.

Zu pathogenen Endoparasiten, bei denen es sich um Helminthen handelt, zählen Plattwürmer (z.B. Monogenea, Cestodes und Trematodes), Rundwürmer, Acanthocephala und Pentastoma. Dazu zählen:

  • Monogenea: z.B.: Gyrodactylus spp., Dactylogyrus spp., Polystoma spp.;
  • Cestodes: aus der Ordnung Pseudophyllidea zum Beispiel: Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., Ligula spp., Bothridium spp., Diplogonoporus spp.;
  • aus der Ordnung Cyclophyllida zum Beispiel: Mesocestoides spp., Anoplocephala spp., Paranoplocephala spp., Moniezia spp., Thysanosoma spp., Thysaniezia spp., Avitellina spp., Stilesia spp., Cittotaenia spp., Andyra spp., Bertiella spp., Taenia spp., Echinococcus spp., Hydatigera spp., Davainea spp., Raillietina spp., Hymenolepis spp., Echinolepis spp., Echinocotyle spp., Diorchis spp., Dipylidium spp., Joyeuxiella spp., Diplopylidium spp.;
  • Trematodes: aus der Klasse Digenea zum Beispiel: Diplostomum spp., Posthodiplostomum spp., Schistosoma spp., Trichobilharzia spp., Ornithobilharzia spp., Austrobilharzia spp., Gigantobilharzia spp., Leucochloridium spp., Brachylaima spp., Echinostoma spp., Echinoparyphium spp., Echinochasmus spp., Hypoderaeum spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Cyclocoelum spp., Typhlocoelum spp., Paramphistomum spp., Calicophoron spp., Cotylophoron spp., Gigantocotyle spp., Fischoederius spp., Gastrothylacus spp., Notocotylus spp., Catatropis spp., Plagiorchis spp., Prosthogonimus spp., Dicrocoelium spp., Eurytrema spp., Troglotrema spp., Paragonimus spp., Collyriclum spp., Nanophyetus spp., Opisthorchis spp., Clonorchis spp. Metorchis spp., Heterophyes spp., Metagonimus spp.;
  • Rundwürmer: Trichinellida zum Beispiel: Trichuris spp., Capillaria spp., Paracapillaria spp., Eucoleus spp., Trichomosoides spp., Trichinella spp.;
  • aus der Ordnung Tylenchida zum Beispiel: Micronema spp., Strongyloides spp.;
  • aus der Ordnung Rhabditida zum Beispiel: Strongylus spp., Triodontophorus spp., Oesophagodontus spp., Trichonema spp., Gyalocephalus spp., Cylindropharynx spp., Poteriostomum spp., Cyclococercus spp., Cylicostephanus spp., Oesophagostomum spp., Chabertia spp., Stephanurus spp., Ancylostoma spp., Uncinaria spp., Necator spp., Bunostomum spp., Globocephalus spp., Syngamus spp., Cyathostoma spp., Metastrongylus spp., Dictyocaulus spp., Muellerius spp., Protostrongylus spp., Neostrongylus spp., Cystocaulus spp., Pneumostrongylus spp., Spicocaulus spp., Elaphostrongylus spp. Parelaphostrongylus spp., Crenosoma spp., Paracrenosoma spp., Oslerus spp., Angiostrongylus spp., Aelurostrongylus spp., Filaroides spp., Parafilaroides spp., Trichostrongylus spp., Haemonchus spp., Ostertagia spp., Teladorsagia spp., Marshallagia spp., Cooperia spp., Nippostrongylus spp., Heligmosomoides spp., Nematodirus spp., Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., Ollulanus spp.;
  • aus der Ordnung Spirurida zum Beispiel: Oxyuris spp., Enterobius spp., Passalurus spp., Syphacia spp., Aspiculuris spp., Heterakis spp.; Ascaris spp., Toxascaris spp., Toxocara spp., Baylisascaris spp., Parascaris spp., Anisakis spp., Ascaridia spp.; Gnathostoma spp., Physaloptera spp., Thelazia spp., Gongylonema spp., Habronema spp., Parabronema spp., Draschia spp., Dracunculus spp.; Stephanofilaria spp., Parafilaria spp., Setaria spp., Loa spp., Dirofilaria spp., Litomosoides spp., Brugia spp., Wuchereria spp., Onchocerca spp., Spirocerca spp.;
  • Acanthocephala: aus der Ordnung Oligacanthorhynchida z.B: Macracanthorhynchus spp., Prosthenorchis spp.; aus der Ordnung Polymorphida zum Beispiel: Filicollis spp.; aus der Ordnung Moniliformida zum Beispiel: Moniliformis spp.;
  • aus der Ordnung Echinorhynchida zum Beispiel Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp.;
  • Pentastoma: aus der Ordnung Porocephalida zum Beispiel Linguatula spp..
Pathogenic endoparasites, which are helminths, include flatworms (eg, Monogenea, Cestodes, and Trematodes), roundworms, Acanthocephala, and Pentastoma. These include:
  • Monogenea: eg: Gyrodactylus spp., Dactylogyrus spp., Polystoma spp .;
  • Cestodes: from the order Pseudophyllidea, for example: Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., Ligula spp., Bothridium spp., Diplogonoporus spp .;
  • from the order Cyclophyllida for example: Mesocestoides spp., Anoplocephala spp., Paranoplocephala spp., Moniezia spp., Thysanosoma spp., Thysaniezia spp., Avitellina spp., Stilesia spp., Cittotaenia spp., Andyra spp., Bertiella spp. , Taenia spp., Echinococcus spp., Hydatigera spp., Davainea spp., Raillietina spp., Hymenolepis spp., Echinolepis spp., Echinocotyle spp., Diorchis spp., Dipylidium spp., Joyeuxiella spp., Diplopylidium spp .;
  • Trematodes: from the genus Digenea, for example: Diplostomum spp., Posthodiplostomum spp., Schistosoma spp., Trichobilharzia spp., Ornithobilharzia spp., Austrobilharzia spp., Gigantobilharzia spp., Leucochloridium spp., Brachylaima spp., Echinostoma spp., Echinoparyphium spp., Echinochasmus spp., Hypoderaeum spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Cyclocoelum spp., Typhlocoelum spp., Paramphistomum spp., Calicophoron spp., Cotylophoron spp., Gigantocotyle spp., Fischoederius spp. , Gastrothylacus spp., Notocotylus spp., Catatropis spp., Plagiorchis spp., Prosthogonimus spp., Dicrocoelium spp., Eurytrema spp., Troglotrema spp., Paragonimus spp., Collyriclum spp., Nanophyetus spp., Opisthorchis spp., Clonorchis spp. Metorchis spp., Heterophyes spp., Metagonimus spp .;
  • Roundworms: Trichinellida for example: Trichuris spp., Capillaria spp., Paracapillaria spp., Eucoleus spp., Trichomosoides spp., Trichinella spp .;
  • from the order Tylenchida for example: Micronema spp., Strongyloides spp .;
  • from the order Rhabditida, for example: Strongylus spp., Triodontophorus spp., Oesophagodontus spp., Trichonema spp., Gyalocephalus spp., Cylindropharynx spp., Poteriostomum spp., Cyclococercus spp., Cylicostephanus spp., Oesophagostomum spp., Chabertia spp. , Stephanurus spp., Ancylostoma spp., Uncinaria spp., Necator spp., Bunostomum spp., Globocephalus spp., Syngamus spp., Cyathostoma spp., Metastrongylus spp., Dictyocaulus spp., Muellerius spp., Protostrongylus spp., Neostrongylus spp., Cystocaulus spp., Pneumostrongylus spp., Spicocaulus spp., Elaphostrongylus spp. Parelaphostrongylus spp., Crenosoma spp., Paracrenosoma spp., Oslerus spp., Angiostrongylus spp., Aelurostrongylus spp., Filaroides spp., Parafilaroides spp., Trichostrongylus spp., Haemonchus spp., Ostertagia spp., Teladorsagia spp., Marshallagia spp , Cooperia spp., Nippostrongylus spp., Heligmosomoides spp., Nematodirus spp., Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., Ollulanus spp .;
  • from the order Spirurida for example: Oxyuris spp., Enterobius spp., Passalurus spp., Syphacia spp., Aspiculuris spp., Heterakis spp .; Ascaris spp., Toxascaris spp., Toxocara spp., Baylisascaris spp., Parascaris spp., Anisakis spp., Ascaridia spp .; Gnathostoma spp., Physaloptera spp., Thelazia spp., Gongylonema spp., Habronema spp., Parabronema spp., Draschia spp., Dracunculus spp .; Stephanofilaria spp., Parafilaria spp., Setaria spp., Loa spp., Dirofilaria spp., Litomosoides spp., Brugia spp., Wuchereria spp., Onchocerca spp., Spirocerca spp .;
  • Acanthocephala: from the order Oligacanthorhynchida eg: Macracanthorhynchus spp., Prosthenorchis spp .; from the order Polymorphida for example: Filicollis spp .; from the order Moniliformida for example: Moniliformis spp .;
  • from the order Echinorhynchida for example Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp .;
  • Pentastoma: from order Porocephalida for example Linguatula spp ..

Auf dem Gebiet der Tiermedizin und der Tierhaltung erfolgt die Verabreichung der Verbindungen der Formel (I) nach allgemein fachbekannten Verfahren, wie enteral, parenteral, dermal oder nasal in Form von geeigneten Präparaten. Die Verabreichung kann prophylaktisch oder therapeutisch erfolgen.In the field of veterinary medicine and animal husbandry, the compounds of the formula (I) are administered by methods well known in the art, such as enteral, parenteral, dermal or nasal in the form of suitable preparations. The administration can be prophylactic or therapeutic.

So bezieht sich eine Ausführungsform der vorliegenden Erfindung auf die Verwendung einer Verbindung der Formel (I) als Arzneimittel.Thus, one embodiment of the present invention relates to the use of a compound of formula (I) as a medicament.

Ein weiterer Aspekt bezieht sich auf die Verwendung einer Verbindung der Formel (I) als Antiendoparasitikum, insbesondere als ein Helminthizid oder ein Mittel gegen Protozoen. Verbindungen der Formel (I) eignen sich für die Verwendung als Antiendoparasitikum, insbesondere als ein Helminthizid oder Mittel gegen Protozoen, beispielsweise in der Tierzucht, in der Tierhaltung, in Ställen und auf dem Hygienesektor.Another aspect relates to the use of a compound of formula (I) as an antiendoparasitic agent, in particular as a helminthicide or antiprotozoal agent. Compounds of the formula (I) are suitable for use as antiendoparasitic agents, in particular as a helminthicide or antiprotozoal agents, for example in animal breeding, animal husbandry, in stables and in the hygiene sector.

Ein weiterer Aspekt wiederum betrifft die Verwendung einer Verbindung der Formel (I) als Antiektoparasitikum, insbesondere ein Arthropodizid wie ein Insektizid oder ein Akarizid Ein weiterer Aspekt betrifft die Verwendung einer Verbindung der Formel (I) als Antiektoparasitikum, insbesondere ein Arthropodizid wie ein Insektizid oder Akarizid, zum Beispiel in der Tierhaltung, in der Tierzucht, in Ställen oder auf dem Hygienesektor.A further aspect in turn relates to the use of a compound of the formula (I) as an antiectica, in particular an arthropodicide such as an insecticide or an acaricide. Another aspect relates to the use of a compound of the formula (I) as anticancer drug, in particular an arthropodicide such as an insecticide or acaricide, for example in animal husbandry, in animal husbandry, in stables or in the hygiene sector.

Vektorkontrollevector control

Die Verbindungen der Formel (I) können auch in der Vektorkontrolle eingesetzt werden. Ein Vektor im Sinne der vorliegenden Erfindung ist ein Arthropode, insbesondere ein Insekt oder Arachnide, der in der Lage ist, Krankheitserreger wie z. B. Viren, Würmer, Einzeller und Bakterien aus einem Reservoir (Pflanze, Tier, Mensch, etc.) auf einen Wirt zu übertragen. Die Krankheitserreger können entweder mechanisch (z.B. Trachoma durch nicht-stechende Fliegen) auf einem Wirt, oder nach Injektion (z.B. Malaria-Parasiten durch Mücken) in einen Wirt übertragen werden.The compounds of formula (I) can also be used in vector control. A vector in the context of the present invention is an arthropod, in particular an insect or arachnid, which is able to attack pathogens such. As viruses, worms, protozoa and bacteria from a reservoir (plant, animal, human, etc.) to a host to transfer. The pathogens may be transferred to a host either mechanically (e.g., trachoma by non-stabbing flies) on a host, or after injection (e.g., malaria parasites by mosquitoes).

Beispiele für Vektoren und die von ihnen übertragenen Krankheiten bzw. Krankheitserreger sind:

  1. 1) Mücken
    • Anopheles: Malaria, Filariose;
    • Culex: Japanische Encephalitis, Filariasis, weitere virale Erkrankungen, Übertragung von Würmern;
    • Aedes: Gelbfieber, Dengue-Fieber, Filariasis, weitere virale Erkrankungen;
    • Simulien: Übertragung von Würmern insbesondere Onchocerca volvulus;
  2. 2) Läuse: Hautinfektionen, Fleckfieber (epidemic typhus);
  3. 3) Flöhe: Pest, endemisches Fleckfieber;
  4. 4) Fliegen: Schlafkrankheit (Trypanosomiasis); Cholera, weitere bakterielle Erkrankungen;
  5. 5) Milben: Acariose, Fleckfieber, Rickettsipocken, Tularämie, Saint-Louis-Enzephalitis, virale Hirnhautentzündung (FSME), Krim-Kongo-Fieber, Borreliose;
  6. 6) Zecken: Borelliosen wie Borrelia duttoni, Frühsommer-Meningoenzephalitis, Q-Fieber (Coxiella burnetii), Babesien (Babesia canis canis).
Examples of vectors and their transmitted diseases or pathogens are:
  1. 1) mosquitoes
    • Anopheles: malaria, filariasis;
    • Culex: Japanese encephalitis, filariasis, other viral diseases, transmission of worms;
    • Aedes: yellow fever, dengue fever, filariasis, other viral diseases;
    • Simulia: transmission of worms, in particular Onchocerca volvulus;
  2. 2) lice: skin infections, typhus (epidemic typhus);
  3. 3) Fleas: plague, endemic typhus fever;
  4. 4) flies: sleeping sickness (trypanosomiasis); Cholera, other bacterial diseases;
  5. 5) mites: acariosis, typhus, rickettsipox, tularemia, Saint-Louis encephalitis, viral meningitis (TBE), Crimean Congo fever, Lyme disease;
  6. 6) Ticks: Borellioses such as Borrelia duttoni, tick-borne encephalitis, Q fever (Coxiella burnetii), Babesia (Babesia canis canis).

Beispiele für Vektoren im Sinne der vorliegenden Erfindung sind Insekten wie Aphiden, Fliegen, Zikaden oder Thripse, die Pflanzenviren auf Pflanzen übertragen können. Weitere Vektoren, die Pflanzenviren übertragen können, sind Spinnmilben, Läuse, Käfer und Nematoden.Examples of vectors in the context of the present invention are insects such as aphids, flies, cicadas or thrips, which can transmit plant viruses to plants. Other vectors that can transmit plant viruses are spider mites, lice, beetles and nematodes.

Weitere Beispiele für Vektoren im Sinne der vorliegenden Erfindung sind Insekten und Arachniden wie Mücken, insbesondere der Gattungen Aedes, Anopheles, z.B. A. gambiae, A. arabiensis, A. funestus, A. dirus (Malaria) und Culex, Läuse, Flöhe, Fliegen, Milben und Zecken, die Krankheitserreger auf Tiere und/oder Menschen übertragen können.Further examples of vectors for the purposes of the present invention are insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, for example A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and culex, lice, fleas, flies, mites and ticks that can transmit pathogens to animals and / or humans.

Eine Vektorkontrolle ist auch möglich, wenn die Verbindungen der Formel (I) Resistenz-brechend sind. Verbindungen der Formel (I) sind zur Verwendung in der Prävention von Krankheiten bzw. vor Krankheitserregern, die durch Vektoren übertragen werden, geeignet. Somit ist ein weiterer Aspekt der vorliegenden Erfindung die nicht therapeutische Verwendung von Verbindungen der Formel (I) zur Vektorkontrolle, z.B. in der Landwirtschaft, im Gartenbau, in Forsten, in Gärten und Freizeiteinrichtungen sowie im Vorrats- und Materialschutz.Vector control is also possible when the compounds of formula (I) are resistance-disrupting. Compounds of formula (I) are suitable for use in the prevention of disease or pathogens transmitted by vectors. Thus, another aspect of the present invention is the non-therapeutic use of compounds of formula (I) for vector control, e.g. in agriculture, horticulture, forests, gardens and recreational facilities, as well as in the protection of materials and materials.

Schutz von technischen MaterialenProtection of technical materials

Die Verbindungen der Formel (I) eignen sich zum Schutz von technischen Materialien gegen Befall oder Zerstörung durch Insekten, z.B. aus der Ordnung Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera und Zygentoma.The compounds of formula (I) are useful for protecting engineering materials against attack or destruction by insects, e.g. from the order Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera and Zygentoma.

Unter technischen Materialien sind im vorliegenden Zusammenhang nicht lebende Materialien zu verstehen, wie vorzugsweise Kunststoffe, Klebstoffe, Leime, Papiere und Kartone, Leder, Holz, Holzverarbeitungsprodukte und Anstrichmittel. Die Anwendung der Erfindung zum Schutz von Holz ist besonders bevorzugt.Technical materials in the present context are non-living materials, such as preferably plastics, adhesives, glues, papers and cardboard, leather, wood, wood processing products and paints. The application of the invention for the protection of wood is particularly preferred.

In einer weiteren Ausführungsform werden die Verbindungen der Formel (I) zusammen mit mindestens einem weiteren Insektizid und/oder mindestens einem Fungizid eingesetzt.In a further embodiment, the compounds of the formula (I) are used together with at least one further insecticide and / or at least one fungicide.

In einer weiteren Ausführungsform liegen die Verbindungen der Formel (I) als ein anwendungsfertiges (ready-to-use) Schädlingsbekämpfungsmittel vor, d.h., es kann ohne weitere Änderungen auf das entsprechende Material aufgebracht werden. Als weitere Insektizide oder als Fungizide kommen insbesondere die oben genannten in Frage.In another embodiment, the compounds of formula (I) are present as a ready-to-use pest control agent, that is, it can be applied to the corresponding material without further changes. As further insecticides or as fungicides in particular the above-mentioned in question.

Überraschenderweise wurde auch gefunden, dass die Verbindungen der Formel (I) zum Schutz vor Bewuchs von Gegenständen, insbesondere von Schiffskörpern, Sieben, Netzen, Bauwerken, Kaianlagen und Signalanlagen, welche mit See- oder Brackwasser in Verbindung kommen, verwendet werden können. Gleichfalls können die Verbindungen der Formel (I) allein oder in Kombinationen mit anderen Wirkstoffen als Antifouling-Mittel eingesetzt werden.Surprisingly, it has also been found that the compounds of the formula (I) can be used to protect against the growth of objects, in particular hulls, sieves, nets, structures, quays and signal systems, which come into contact with seawater or brackish water. Likewise, the compounds of the formula (I) can be used alone or in combination with other active substances as antifouling agents.

Bekämpfung von tierischen Schädlingen auf dem HygienesektorControl of animal pests in the hygiene sector

Die Verbindungen der Formel (I) eignen sich zur Bekämpfung von tierischen Schädlingen auf dem Hygienesektor. Insbesondere kann die Erfindung im Haushalts-, Hygiene- und Vorratsschutz verwendet werden, vor allem zur Bekämpfung von Insekten, Spinnentieren und Milben, die in geschlossenen Räumen, wie beispielsweise Wohnungen, Fabrikhallen, Büros, Fahrzeugkabinen vorkommen. Zur Bekämpfung der tierischen Schädlinge werden die Verbindungen der Formel (I) allein oder in Kombination mit anderen Wirk- und/oder Hilfsstoffen verwendet. Bevorzugt werden sie in Haushaltsinsektizid-Produkten verwendet. Die Verbindungen der Formel (I) sind gegen sensible und resistente Arten sowie gegen alle Entwicklungsstadien wirksam.The compounds of the formula (I) are suitable for controlling animal pests in the hygiene sector. In particular, the invention can be used in household, hygiene and storage protection, especially for controlling insects, arachnids and mites, which occur in enclosed spaces, such as apartments, factories, offices, vehicle cabins. to To combat animal pests, the compounds of formula (I) are used alone or in combination with other active ingredients and / or adjuvants. Preferably, they are used in household insecticide products. The compounds of formula (I) are active against sensitive and resistant species and against all stages of development.

Zu diesen Schädlingen gehören beispielsweise Schädlinge aus der Klasse Arachnida, aus den Ordnungen Scorpiones, Araneae und Opiliones, aus den Klassen Chilopoda und Diplopoda, aus der Klasse Insecta die Ordnung Blattodea, aus den Ordnungen Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera, Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria oder Orthoptera, Siphonaptera und Zygentoma und aus der Klasse Malacostraca die Ordnung Isopoda.These pests include, for example, pests of the class Arachnida, from the orders Scorpiones, Araneae and Opiliones, from the classes Chilopoda and Diplopoda, from the class Insecta the order Blattodea, from the orders Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera, Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria or Orthoptera, Siphonaptera and Zygentoma and from the class Malacostraca the order Isopoda.

Die Anwendung erfolgt beispielsweise in Aerosolen, drucklosen Sprühmitteln, z.B. Pump- und Zerstäubersprays, Nebelautomaten, Foggern, Schäumen, Gelen, Verdampferprodukten mit Verdampferplättchen aus Cellulose oder Kunststoff, Flüssigverdampfern, Gel- und Membranverdampfern, propellergetriebenen Verdampfern, energielosen bzw. passiven Verdampfungssystemen, Mottenpapieren, Mottensäckchen und Mottengelen, als Granulate oder Stäube, in Streuködern oder Köderstationen.Application is for example in aerosols, non-pressurized sprays, e.g. Pump and atomizer sprays, misting machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller driven evaporators, energyless or passive evaporation systems, moth papers, moth cakes and moth gels, as granules or dusts, in litter or bait stations.

Erläuterung der Verfahren und ZwischenprodukteExplanation of processes and intermediates

Die folgenden Herstellungs- bzw. Synthese- und Verwendungsbeispiele illustrieren die Erfindung, ohne sie zu beschränken. Die Produkte wurden mittels 1H-NMR Spektroskopie und/oder LC/MS (Liquid Chromatography Mass Spectrometry) charakterisiert.The following preparation or synthesis and use examples illustrate the invention without limiting it. The products were characterized by 1 H NMR spectroscopy and / or LC / MS (Liquid Chromatography Mass Spectrometry).

Die Bestimmung der logP Werte erfolgte gemäß OECD Guideline 117 (EC Directive 92/69/EEC) durch HPLC (High Performance Liquid Chromatography) an reversed-phase (RP) Säulen (C18), mit nachfolgenden Methoden:

  1. [a] Die Bestimmung mit der LC-MS im sauren Bereich erfolgt bei pH 2,7 mit 0,1 % wässriger Ameisensäure und Acetonitril (enthält 0,1% Ameisensäure) als Eluenten; linearer Gradient von 10% Acetonitril bis 95% Acetonitril.
  2. [b] Die Bestimmung mit der LC-MS im neutralen Bereich erfolgt bei pH 7.8 mit 0,001 molarer wässriger Ammoniumhydrogencarbonat-Lösung und Acetonitril als Eluenten; linearer Gradient von 10 % Acetonitril bis 95 % Acetonitril.
The determination of the logP values was carried out according to OECD Guideline 117 (EC Directive 92/69 / EEC) by HPLC (High Performance Liquid Chromatography) on reversed-phase (RP) columns (C18), using the following methods:
  1. [a] The determination with the LC-MS in the acidic range is carried out at pH 2.7 with 0.1% aqueous formic acid and acetonitrile (containing 0.1% formic acid) as eluent; linear gradient from 10% acetonitrile to 95% acetonitrile.
  2. [b] The determination with the LC-MS in the neutral range is carried out at pH 7.8 with 0.001 molar aqueous ammonium bicarbonate solution and acetonitrile as eluent; linear gradient from 10% acetonitrile to 95% acetonitrile.

Die Eichung erfolgt mit unverzweigten Alkan-2-onen (mit 3 bis 16 Kohlenstoffatomen), deren logP-Werte bekannt sind (Bestimmung der logP-Werte anhand der Retentionszeiten durch lineare Interpolation zwischen zwei aufeinander folgenden Alkanonen).The calibration is carried out with unbranched alkan-2-ones (with 3 to 16 carbon atoms), whose logP values are known (determination of the logP values by means of the retention times by linear interpolation between two consecutive alkanones).

Die NMR-Spektren wurden mit einem Bruker Avance 400, ausgestattet mit einem Durchflussprobenkopf (60 µl Volumen), bestimmt. In Einzelfällen wurden die NMR Spektren mit einem Bruker Avance II 600 gemessen.The NMR spectra were determined on a Bruker Avance 400 equipped with a flow-through head (60 μl volume). In individual cases the NMR spectra were measured with a Bruker Avance II 600.

Die 1H-NMR-Daten ausgewählter Beispiele werden in Form von 1H-NMR-Peaklisten notiert. Zu jedem Signalpeak wird erst der □-Wert in ppm und dann die Signalintensität in runden Klammern aufgeführt. Die □-Wert - Signalintensitäts- Zahlenpaare von verschiedenen Signalpeaks werden durch Semikolons voneinander getrennt aufgelistet.The 1 H NMR data of selected examples are noted in terms of 1 H NMR peaks. For each signal peak, first the □ -value in ppm and then the signal intensity in round brackets are listed. The □ value - signal intensity number pairs of different signal peaks are listed separated by semicolons.

Die Peakliste eines Beispieles hat daher die Form:
□1 (Intensität 1); □2 (Intensität 2);........; □i (Intensität i);......; □n (Intensität n)The peak list of an example therefore has the form:
□ 1 (intensity 1); □ 2 (intensity 2); ........; □ i (intensity i); ......; □ n (intensity n)

Die Intensität scharfer Signale korreliert mit der Höhe der Signale in einem gedruckten Beispiel eines NMR-Spektrums in cm und zeigt die wirklichen Verhältnisse der Signalintensitäten. Bei breiten Signalen können mehrere Peaks oder die Mitte des Signals und ihre relative Intensität im Vergleich zum intensivsten Signal im Spektrum gezeigt werden.The intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. For broad signals, multiple peaks or the center of the signal and their relative intensity can be shown compared to the most intense signal in the spectrum.

Zur Kalibrierung der chemischen Verschiebung von 1H-NMR-Spektren benutzen wir Tetramethylsilan und/oder die chemische Verschiebung des Lösungsmittels, besondern im Falle von Spektren, die in DMSO gemessen werden. Daher kann in NMR-Peaklisten der Tetramethylsilan-Peak vorkommen, muss es aber nicht.To calibrate the chemical shift of 1 H NMR spectra we use tetramethylsilane and / or the chemical shift of the solvent, especially in the case of spectra measured in DMSO. Therefore, the tetramethylsilane peak can occur in NMR peaks, but it does not have to.

Die Listen der 1H-NMR-Peaks sind ähnlich den klassischen 1H-NMR-Ausdrucken und enthalten somit gewöhnlich alle Peaks, die bei einer klassischen NMR-Interpretation aufgeführt werden.The lists of the 1 H NMR peaks are similar to the classical 1 H NMR prints and thus usually contain all the peaks listed in a classical NMR interpretation.

Darüber hinaus können sie wie klassische 1H-NMR-Ausdrucke Lösungsmittelsignale, Signale von Stereoisomeren der Zielverbindungen, die ebenfalls Gegenstand der Erfindung sind, und/oder Peaks von Verunreinigungen zeigen.Moreover, like classical 1 H NMR prints, they can show solvent signals, signals from stereoisomers of the target compounds, which are also the subject of the invention, and / or peaks of impurities.

Bei der Angabe von Verbindungssignalen im Delta-Bereich von Lösungsmitteln und/oder Wasser sind in unseren Listen von 1H-NMR-Peaks die gewöhnlichen Lösungsmittelpeaks, zum Beispiel Peaks von DMSO in DMSO-D6 und der Peak von Wasser, gezeigt, die gewöhnlich im Durchschnitt eine hohe Intensität aufweisen.When indicating compound signals in the delta range of solvents and / or water, our lists of 1 H NMR peaks show the usual solvent peaks, for example peaks of DMSO in DMSO-D 6 and the peak of water, which are usually on average have a high intensity.

Die Peaks von Stereoisomeren der Targetverbindungen und/oder Peaks von Verunreinigungen haben gewöhnlich im Durchschnitt eine geringere Intensität als die Peaks der Zielverbindungen (zum Beispiel mit einer Reinheit von >90%).The peaks of stereoisomers of the target compounds and / or peaks of impurities usually have on average a lower intensity than the peaks of the target compounds (for example with a purity of> 90%).

Solche Stereoisomere und/oder Verunreinigungen können typisch für das jeweilige Herstellungsverfahren sein. Ihre Peaks können somit dabei helfen, die Reproduktion unseres Herstellungsverfahrens anhand von "Nebenprodukt-Fingerabdrücken" zu erkennen.Such stereoisomers and / or impurities may be typical of the particular preparation process. Their peaks can thus help identify the reproduction of our manufacturing process by "by-product fingerprints."

Einem Experten, der die Peaks der Zielverbindungen mit bekannten Verfahren (MestreC, ACD-Simulation, aber auch mit empirisch ausgewerteten Erwartungswerten) berechnet, kann je nach Bedarf die Peaks der Zielverbindungen isolieren, wobei gegebenenfalls zusätzliche Intensitätsfilter eingesetzt werden. Diese Isolierung wäre ähnlich dem betreffenden Peak-Picking bei der klassischen 1H-NMR-Interpretation.An expert calculating the peaks of the target compounds by known methods (MestreC, ACD simulation, but also with empirically evaluated expectation values) can isolate the peaks of the target compounds as needed, using additional intensity filters if necessary. This isolation would be similar to peak-picking in classical 1 H NMR interpretation.

Weitere Details zu 1H-NMR-Peaklisten können der Research Disclosure Database Number 564025 entnommen werden.Further details on 1 H NMR peaks can be obtained from the Research Disclosure Database Number 564025 be removed.

Synthesen von 5-substituierten 2-(3-Pyridyl)-thiazo[5,4-b]pyridinenSyntheses of 5-substituted 2- (3-pyridyl) thiazo [5,4-b] pyridines Synthese von 5-Chlor-2-(3-pyridyl)thiazolo[5,4-b]pyridinSynthesis of 5-chloro-2- (3-pyridyl) thiazolo [5,4-b] pyridine Schritt 1: N-(2,6-Dichlor-3-pyridyl)pyridin-3-carboxamid Step 1: N - (2,6-dichloro-3-pyridyl) pyridine-3-carboxamide

Figure imgb0273
Figure imgb0273

Zu einer Lösung von 3-Amino-2,6-dichlorpyridin (5,00 g, 30,7 mmol) in Acetonitril (120 mL) und Pyridin (20 mL) wurde bei 0 °C eine Suspension von Pyridin-3-carbonsäurechlorid-Hydrochlorid (16,4 g, 92,0 mmol) in Acetonitril (300 mL) gegeben. Die Reaktionsmischung wurde für 16 h bei Raumtemperatur gerührt. Anschließend wurde sie mit Wasser vesetzt, mit Natronlauge (1 M) alkalisch gestellt und mit Ethylacetat extrahiert. Die vereinigten organischen Phasen wurden mit Na2SO4 getrocknet und das Lösungmittel unter reduziertem Druck entfernt. So wurden 7,64 g (100% Reinheit, 93% Ausbeute) des N-(2,6-Dichlor-3-pyridyl)pyridin-3-carboxamids erhalten.
1H-NMR(400,0 MHz, d6-DMSO): δ = 9,143(10,4); 9,138(10,3); 8,814(6,9); 8,810(7,7); 8,802(7,4); 8,798(7,6); 8,341(4,0); 8,336(6,2); 8,331(4,3); 8,321(4,4); 8,316(6,8); 8,311(4,4); 8,192 (4,4); 8,171(15,9); 7,683 (16,0); 7,662 (14,9); 7,621(5,6); 7,609(5,5); 7,601(5,4); 7,589(5,1); 3,335(158,4); 2,677(0,6); 2,672(0,8); 2,668(0,6); 2,526(2,0); 2,508(86,2); 2,503(113,2); 2,499(85,0); 2,335(0,5); 2,330(0,7); 2,326(0,5); 1,990(0,5); 1,259(0,4); 1,234(2,9); 0,008(0,9); -0,000(25,7); -0,008(1,1).To a solution of 3-amino-2,6-dichloropyridine (5.00 g, 30.7 mmol) in acetonitrile (120 mL) and pyridine (20 mL) at 0 ° C was added a suspension of pyridine-3-carboxylic acid chloride. Hydrochloride (16.4 g, 92.0 mmol) in acetonitrile (300 mL). The reaction mixture was stirred for 16 h at room temperature. It was then used with water, made alkaline with sodium hydroxide solution (1 M) and extracted with ethyl acetate. The combined organic phases were dried with Na 2 SO 4 and the solvent removed under reduced pressure. Thus, 7.64 g (100% purity, 93% yield) of N - receive (2,6-dichloro-3-pyridyl) pyridine-3-carboxamide.
1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.143 (10.4); 9.138 (10.3); 8,814 (6.9); 8,810 (7.7); 8,802 (7.4); 8,798 (7.6); 8,341 (4.0); 8,336 (6.2); 8,331 (4.3); 8,321 (4.4); 8,316 (6.8); 8,311 (4.4); 8,192 (4.4); 8,171 (15.9); 7,683 (16.0); 7,662 (14.9); 7.621 (5.6); 7,609 (5.5); 7,601 (5.4); 7,589 (5.1); 3.335 (158.4); 2,677 (0.6); 2,672 (0.8); 2,668 (0.6); 2,526 (2.0); 2,508 (86.2); 2.503 (113.2); 2,499 (85.0); 2,335 (0.5); 2,330 (0.7); 2,326 (0.5); 1,990 (0.5); 1,259 (0.4); 1,234 (2.9); 0.008 (0.9); -0.000 (25.7); -0.008 (1,1).

Schritt 2: 5-Chlor-2-(3-pyridyl)thiazolo[5,4-b]pyridin Step 2: 5-Chloro-2- (3-pyridyl) thiazolo [5,4-b] pyridine

Figure imgb0274
Figure imgb0274

Eine Suspension von N-(2,6-Dichlor-3-pyridyl)pyridin-3-carboxamid (881 mg, 3,28 mmol) und 2,4-Bis-(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetan-2,4-disulfid (1,37 g, 3,28 mmol) in Toluol (37 mL) wurde insgesamt 13 h unter Rückfluss und weitere 32 h bei 100 °C gerührt. Anschließend wurde das Lösungsmittel unter reduziertem Druck entfernt und der Rückstand mit CH2Cl2 und gesättiger NaHCO3-Lösung versetzt. Die Phasen wurden getrennt, die wässrige Phase mit CH2Cl2 extrahiert und die vereinigten organischen Phasen mit Na2SO4 getrocknet. Nach dem Entfernen des Lösungsmittels unter reduziertem Druck wurde der Rückstand mittels MPLC an Kieselgel chromatographisch aufgetrennt (Gradient: Ethylacetat/Cyclohexan 0:100 → 30:70). So wurden 325 mg (98% Reinheit, 39% Ausbeute) des 5-Chlor-2-(3-pyridyl)thiazolo[5,4-b]pyridins erhalten.
1H-NMR(400,0 MHz, d6-DMSO): δ = 9,302(6,3); 9,300(7,0); 9,296(6,9); 9,294(6,7); 8,814(6,0); 8,810(6,6); 8,802(6,4); 8,798(6,5); 8,579(15,0); 8,558(15,8); 8,506(3,9); 8,502(4,6); 8,500(4,6); 8,496(3,9); 8,486(4,1); 8,482(4,6); 8,480(5,0); 8,476(3,9); 8,318(0,5); 7,761(16,0); 7,740(15,1); 7,672(4,6); 7,670(4,9); 7,660(4,5); 7,658(4,7); 7,652(4,4); 7,650(4,6); 7,640(4,3); 7,638(4,5); 3,330(93,2); 2,682(0,4); 2,677(0,8); 2,673(1,1); 2,668(0,8); 2,664(0,4); 2,526(2,7); 2,521(4,0); 2,513(58,2); 2,508(121,6); 2,503(164,7); 2,499(121,9); 2,494(59,5); 2,339(0,4); 2,335(0,8); 2,330(1,1); 2,326(0,8); 2,321(0,4); 1,398(1,6); 1,231(0,4); 0,000(1,0).A suspension of N - (2,6-dichloro-3-pyridyl) pyridine-3-carboxamide (881 mg, 3.28 mmol) and 2,4-bis (4-methoxyphenyl) -1,3,2,4 -dithiadiphosphetane-2,4-disulfide (1.37 g, 3.28 mmol) in toluene (37 mL) was stirred at reflux for a total of 13 h and at 100 ° C for a further 32 h. Then the solvent was removed under reduced pressure and the residue with CH 2 Cl 2 and saturated NaHCO 3 solution was added. The phases were separated, the aqueous phase extracted with CH 2 Cl 2 and the combined organic phases dried with Na 2 SO 4 . After removing the solvent under reduced pressure, the residue was chromatographed on silica gel by MPLC (gradient: ethyl acetate / cyclohexane 0: 100 → 30:70). Thus, 325 mg (98% purity, 39% yield) of 5-chloro-2- (3-pyridyl) thiazolo [5,4-b] pyridine was obtained.
1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.302 (6.3); 9,300 (7.0); 9,296 (6.9); 9,294 (6.7); 8,814 (6.0); 8,810 (6.6); 8,802 (6.4); 8,798 (6.5); 8,579 (15.0); 8,558 (15.8); 8,506 (3.9); 8,502 (4.6); 8,500 (4.6); 8,496 (3.9); 8.486 (4.1); 8,482 (4.6); 8,480 (5.0); 8,476 (3.9); 8,318 (0.5); 7,761 (16.0); 7,740 (15.1); 7,672 (4.6); 7,670 (4.9); 7,660 (4.5); 7,658 (4.7); 7,652 (4.4); 7,650 (4.6); 7,640 (4.3); 7.638 (4.5); 3,330 (93.2); 2,682 (0.4); 2,677 (0.8); 2,673 (1.1); 2,668 (0.8); 2,664 (0.4); 2,526 (2.7); 2,521 (4.0); 2,513 (58.2); 2,508 (121.6); 2.503 (164.7); 2.499 (121.9); 2,494 (59.5); 2,339 (0.4); 2,335 (0.8); 2,330 (1.1); 2,326 (0.8); 2,321 (0.4); 1,398 (1.6); 1,231 (0.4); 0.000 (1.0).

Synthese von 2-(3-Pyridyl)-5-(trifluormethyl)thiazolo[5,4-b]pyridin (Beispiel 10)Synthesis of 2- (3-pyridyl) -5- (trifluoromethyl) thiazolo [5,4-b] pyridine (Example 10) Schritt 1: N-[2-Chlor-6-(trifluormethyl)-3-pyridyl]pyridin-3-carboxamid Step 1: N - [2-Chloro-6- (trifluoromethyl) -3-pyridyl] pyridine-3-carboxamide

Figure imgb0275
Figure imgb0275

Die Herstellung des N-[2-Chlor-6-(trifluormethyl)-3-pyridyl]pyridin-3-carboxamids erfolgte in Analogie zur Synthese des N-(2,6-Dichlor-3-pyridyl)pyridin-3-carboxamids. Dazu wurde eine Lösung von 2-Chlor-6-(trifluormethyl)pyridin-3-amin (200 mg, 1,02 mmol), Pyridin-3-carbonsäurechlorid-Hydrochlorid (543 mg, 3,05 mmol) und Pyridin (0,66 mL, 8,1 mmol) in Acetonitril für 31 h bei Raumtemperatur gerührt. Es wurden 218 mg (100% Reinheit, 71% Ausbeute) des N-[2-Chlor-6-(trifluormethyl)-3-pyridyl]pyridin-3-carboxamid erhalten.
1H-NMR(400,0 MHz, d6-DMSO): δ = 10,696(12,3); 9,156 (12,2); 9,152(12,3); 8,833(8,6); 8,829(9,1); 8,821(9,3); 8,817(8,9); 8,482(9,6); 8,461(10,8); 8,359(5,2); 8,354(7,1); 8,349(5,2); 8,339(5,7); 8,334(7,4); 8,329(5,3); 8,318(0,6); 8,076(16,0); 8,056(14,6); 7,640(6,2); 7,639(6,2); 7,628(6,3); 7,627(6,3); 7,621(6,3); 7,619(6,1); 7,609(5,9); 7,607(5,7); 4,021(0,3); 3,333(126,0); 2,677(0,8); 2,673 (1,1); 2,668(0,8); 2,526(3,0); 2,512(63,3); 2,508(121,9); 2,504(155,9); 2,499(115,8); 2,495(59,2); 2,335(0,8); 2,33(1,0); 2,326(0,8); 1,990(1,4); 1,193(0,4); 1,176(0,7); 1,158(0,4); 0,008(1,6);-0,000(37,8); -0,008(2,0).The preparation of N- [2-chloro-6- (trifluoromethyl) -3-pyridyl] pyridine-3-carboxamide was carried out in analogy to the synthesis of N - (2,6-dichloro-3-pyridyl) pyridine-3-carboxamide. To this was added a solution of 2-chloro-6- (trifluoromethyl) pyridin-3-amine (200 mg, 1.02 mmol), pyridine-3-carboxylic acid chloride hydrochloride (543 mg, 3.05 mmol) and pyridine (0, 66 mL, 8.1 mmol) in acetonitrile for 31 h at room temperature. There were obtained 218 mg (100% purity, 71% yield) of N - [2-chloro-6- (trifluoromethyl) -3-pyridyl] pyridine-3-carboxamide.
1 H NMR (400.0 MHz, d 6 -DMSO): δ = 10.696 (12.3); 9,156 (12,2); 9,152 (12.3); 8.833 (8.6); 8.829 (9.1); 8,821 (9.3); 8.817 (8.9); 8,482 (9.6); 8.461 (10.8); 8,359 (5.2); 8,354 (7.1); 8,349 (5.2); 8,339 (5.7); 8,334 (7.4); 8.329 (5.3); 8,318 (0.6); 8,076 (16.0); 8.056 (14.6); 7,640 (6.2); 7,639 (6.2); 7.628 (6.3); 7.627 (6.3); 7.621 (6.3); 7,619 (6.1); 7,609 (5.9); 7,607 (5.7); 4,021 (0.3); 3.333 (126.0); 2,677 (0.8); 2,673 (1.1); 2,668 (0.8); 2,526 (3.0); 2,512 (63.3); 2,508 (121.9); 2.504 (155.9); 2.499 (115.8); 2,495 (59.2); 2,335 (0.8); 2.33 (1.0); 2,326 (0.8); 1,990 (1.4); 1.193 (0.4); 1,176 (0.7); 1,158 (0.4); 0,008 (1.6) - 0,000 (37.8); -0.008 (2.0).

Schritt 2: 2-(3-Pyridyl)-5-(trifluormethyl)thiazolo[5,4-b]pyridin (Beispiel 10) Step 2: 2- (3-Pyridyl) -5- (trifluoromethyl) thiazolo [5,4-b] pyridine (Example 10)

Figure imgb0276
Figure imgb0276

Die Herstellung des 2-(3-Pyridyl)-5-(trifluormethyl)thiazolo[5,4-b]pyridins erfolgte in Analogie zur Synthese des 5-Chlor-2-(3-pyridyl)thiazolo[5,4-b]pyridin. Dabei wurde eine Mischung von N-[2-Chlor-6-(trifluormethyl)-3-pyridyl]pyridin-3-carboxamid (206 mg, 683 µmol), 2,4-Bis-(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetan-2,4-disulfid (283 mg, 700 µmol) und Toluol (20 mL) für 16 h bei 100 °C und weitere 5 h unter Rückfluss gerührt. Es wurden 116 mg (100% Reinheit, 60% Ausbeute) des 2-(3-Pyridyl)-5-(trifluormethyl)thiazolo[5,4-b]pyridins erhalten.
1H-NMR(400,0 MHz, d6-DMSO): δ = 9,354(8,2); 9,352(8,9); 9,348(8,9); 9,346(8,5); 8,849(7,2); 8,845(7,8); 8,837(7,7); 8,833(7,7); 8,781(8,4); 8,780(8,4); 8,760(9,1); 8,759(9,0); 8,561(4,4); 8,557(5,5); 8,556(5,3); 8,551(4,4); 8,541(4,8); 8,537(5,5); 8,535(5,8); 8,531(4,5); 8,151(16,0); 8,130(15,0); 7,700(5,4); 7,698(5,5); 7,688(5,2); 7,686(5,3); 7,680(5,2); 7,678(5,2); 7,668(5,1); 7,666(5,1); 3,338(38,7); 2,681(0,3); 2,677(0,5); 2,672(0,3); 2,530(1,2); 2,525(1,7); 2,517(26,2); 2,512(54,4); 2,508(72,0); 2,503(51,8); 2,499(24,7); 2,339(0,3); 2,334(0,5); 2,330(0,3); 1,993(0,4); 1,225(1,4); 0,008(0,9); 0,000(30,6); -0,009(1,0).The preparation of 2- (3-pyridyl) -5- (trifluoromethyl) thiazolo [5,4-b] pyridine was carried out in analogy to the synthesis of the 5-chloro-2- (3-pyridyl) thiazolo [5,4-b] pyridine. A mixture of N - [2-chloro-6- (trifluoromethyl) -3-pyridyl] pyridine-3-carboxamide (206 mg, 683 μmol), 2,4-bis (4-methoxyphenyl) -1,3 was added , 2,4-dithiadiphosphetane-2,4-disulfide (283 mg, 700 .mu.mol) and toluene (20 mL) for 16 h at 100 ° C and stirred for a further 5 h under reflux. 116 mg (100% purity, 60% yield) of 2- (3-pyridyl) -5- (trifluoromethyl) thiazolo [5,4-b] pyridine were obtained.
1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.354 (8.2); 9,352 (8.9); 9,348 (8.9); 9,346 (8.5); 8.849 (7.2); 8,845 (7.8); 8,837 (7.7); 8.833 (7.7); 8.781 (8.4); 8,780 (8.4); 8,760 (9.1); 8.759 (9.0); 8.561 (4.4); 8,557 (5.5); 8,556 (5.3); 8,551 (4.4); 8,541 (4.8); 8,537 (5.5); 8,535 (5.8); 8,531 (4.5); 8,151 (16.0); 8,130 (15.0); 7,700 (5.4); 7.698 (5.5); 7.688 (5.2); 7.686 (5.3); 7,680 (5.2); 7,678 (5.2); 7.668 (5.1); 7,666 (5.1); 3.338 (38.7); 2,681 (0.3); 2,677 (0.5); 2,672 (0.3); 2,530 (1.2); 2,525 (1.7); 2,517 (26.2); 2,512 (54.4); 2,508 (72.0); 2,503 (51.8); 2,499 (24.7); 2,339 (0.3); 2,334 (0.5); 2,330 (0.3); 1,993 (0.4); 1,225 (1.4); 0.008 (0.9); 0,000 (30.6); -0.009 (1.0).

Synthese von Methyl-2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin-5-carboxylatSynthesis of methyl 2- (pyridin-3-yl) [1,3] thiazolo [5,4-b] pyridine-5-carboxylate Schritt 1: N-(2,6-Dibrompyridin-3-yl)nicotinamid Step 1: N - (2,6-Dibromopyridin-3-yl) nicotinamide

Figure imgb0277
Figure imgb0277

Zu einer Lösung von Pyridin-3-carbonsäure (9.77 g, 79,4 mmol) in CH2Cl2 (500 mL) wurden bei 0 °C Pyridin (18,84 g, 238,17 mmol) und (Chlormethylene)dimethylammoniumchlorid (15.24 g, 119,1 mmol) gegeben. Die Mischung wurde für 30 min bei 0 °C gerührt und dann 2,6-Dibrompyridin-3-amin (20,0 g, 79,4 mmol) hinzugefügt. Die Reaktionsmischung wurde für 16 h bei Raumtemperatur gerührt, zu einer gesättigen NaHCO3-Lösung gegeben (500 mL) und mit CH2Cl2 (2x500 mL) extrahiert. Die vereinigten organischen Phasen wurden mit Wasser (300 mL) und gesättigter Kochsalzlösung (300 mL) gewaschen, mit Natriumsulfat getrocknet, filtriert und das Lösungsmittel unter reduziertem Druck entfernt. Der Rückstand wurde mittels Säulenchromatographie an Kieselgel chromatographisch aufgetrennt (Gradient: Ethylacetat/Petrolether 20:80 → 33:66). So wurden 15,0 g (53% Ausbeute) des N-(2,6-Dibrompyridin-3-yl)nicotinamids erhalten.To a solution of pyridine-3-carboxylic acid (9.77 g, 79.4 mmol) in CH 2 Cl 2 (500 mL) at 0 ° C was pyridine (18.84 g, 238.17 mmol) and (chloromethylene) dimethylammonium chloride ( 15.24 g, 119.1 mmol). The mixture was stirred for 30 min at 0 ° C and then 2,6-dibromopyridin-3-amine (20.0 g, 79.4 mmol) was added. The reaction mixture was stirred for 16 h at room temperature, added to a saturated NaHCO 3 solution (500 mL) and extracted with CH 2 Cl 2 (2x500 mL). The combined organic phases were washed with water (300 mL) and brine (300 mL), dried with sodium sulfate, filtered and the solvent removed under reduced pressure. The residue was chromatographed by column chromatography on silica gel (gradient: ethyl acetate / petroleum ether 20:80 → 33:66). Thus, 15.0 g (53% yield) of N - (2,6-dibromopyridin-3-yl) nicotinamide was obtained.

Schritt 2: 5-Brom-2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin Step 2: 5-Bromo-2- (pyridin-3-yl) [1,3] thiazolo [5,4-b] pyridine

Figure imgb0278
Figure imgb0278

Eine Mischung von N-(2,6-Dibrompyridin-3-yl)nicotinamid (20,0 g, 56,0 mmol) und 2,4-Bis-(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetan-2,4-disulfid (33,99 g, 84,03 mmol) in 1,4-Dioxan (300 mL) wurde für 3 h bei 110 °C gerührt. Das Lösungsmittel wurde anschließend unter reduziertem Druck entfernt und der Rückstand mit Ethylacetat (150 mL) und Dimethylformamid (30 mL) gewaschen. So wurden 13,0 g (79% Ausbeute) 5-Brom-2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin erhalten.A mixture of N - (2,6-dibromopyridin-3-yl) nicotinamide (20.0 g, 56.0 mmol) and 2,4-bis (4-methoxyphenyl) -1,3,2,4-dithiadiphosphetane -2,4-disulfide (33.99 g, 84.03 mmol) in 1,4-dioxane (300 mL) was stirred for 3 h at 110 ° C. The solvent was then removed under reduced pressure and the residue washed with ethyl acetate (150 mL) and dimethylformamide (30 mL). There was thus obtained 13.0 g (79% yield) of 5-bromo-2- (pyridin-3-yl) [1,3] thiazolo [5,4-b] pyridine.

Schritt 3: Methyl-2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin-5-carboxylat Step 3 : Methyl 2- (pyridin-3-yl) [1,3] thiazolo [5,4-b] pyridine-5-carboxylate

Figure imgb0279
Figure imgb0279

Zu einer Lösung von 5-Brom-2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin (13,0 g, 44,5 mmol) in THF (300 mL), Dimethylformamid (150 mL) und Methanol (150 mL) wurden Triethylamin (13,5 g, 133 mmol) und 1,1'-Bis(diphenylphosphino)ferrocene]dichlorpalladium(II) 6,51 g, 8,90 mmol) gegeben. Die Reaktionsmischung wurde bei 70 °C für 16 h unter einer Atmosphäre von Kohlenmonoxid (3,1 bar) gerührt und anschließend die Lösungsmittel unter reduziertem Druck entfernt. Der Rückstand wurde mittels Säulenchromatographie an Kieselgel chromatographisch aufgetrennt (Gradient: Ethylacetat/Petrolether 50:50 → 66:33). So wurden 4,0 g (33% Ausbeute) des Methyl-2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin-5-carboxylats erhalten.
MS: m/z 272,0 [M+H+]To a solution of 5-bromo-2- (pyridin-3-yl) [1,3] thiazolo [5,4-b] pyridine (13.0 g, 44.5 mmol) in THF (300 mL), dimethylformamide (150 mL) and methanol (150 mL) were added triethylamine (13.5 g, 133 mmol) and 1,1'-bis (diphenylphosphino) ferrocenes] dichloropalladium (II) 6.51 g, 8.90 mmol). The reaction mixture was stirred at 70 ° C for 16 h under an atmosphere of carbon monoxide (3.1 bar) and then the solvents were removed under reduced pressure. The residue was chromatographed by column chromatography on silica gel (gradient: ethyl acetate / petroleum ether 50:50 → 66:33). There was thus obtained 4.0 g (33% yield) of the methyl 2- (pyridin-3-yl) [1,3] thiazolo [5,4-b] pyridine-5-carboxylate.
MS: m / z 272.0 [M + H + ]

Allgemeine Vorschrift zur Synthese von Amiden der 2-(Pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin-5-carbonsäureGeneral procedure for the synthesis of amides of 2- (pyridin-3-yl) [1,3] thiazolo [5,4-b] pyridine-5-carboxylic acid

Figure imgb0280
Figure imgb0280

Eine Lösung von Methyl-2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin-5-carboxylat (300 mg, 1,11 mmol) und Kaliumtrimethylsilanolat (171 mg, 1,33 mmol) in THF (8 mL) wurde für 16 h bei 30 °C gerührt. Das Lösungsmittel wurde unter reduziertem Druck entfernt und der Rückstand in Dimethylformamid (5 mL) aufgenommen. Zu dieser Lösung wurden 1-[bis(Dimethylamin)methylen]-1H-1,2,3-triazol[4,5-b]pyridinium-3-oxid-hexafluorophosphat (422 mg, 1,33 mmol) und Ethyldiisopropylamine (0,58 mL, 3,33 mmol) gegeben und das Gemisch für 30 min bei 30 °C gerührt. Anschließend wurde das jeweilige Amin (1,33 mmol) hinzugefügt, für weitere 16 h bei 30 °C gerührt und das Lösungsmittel unter reduziertem Druck entfernt. Zur Isolation des Produkts wurde die Reaktionsmischung per HPLC aufgereinigt.A solution of methyl 2- (pyridin-3-yl) [1,3] thiazolo [5,4-b] pyridine-5-carboxylate (300 mg, 1.11 mmol) and potassium trimethylsilanolate (171 mg, 1.33 mmol) in THF (8 mL) was stirred for 16 h at 30 ° C. The solvent was removed under reduced pressure and the residue taken up in dimethylformamide (5 mL). To this solution was added 1- [bis (dimethylamine) methylene] -1H-1,2,3-triazolo [4,5-b] pyridinium 3-oxide hexafluorophosphate (422 mg, 1.33 mmol) and ethyldiisopropylamine (0 , 58 mL, 3.33 mmol) and the mixture was stirred for 30 min at 30 ° C. Then the respective amine (1.33 mmol) was added, stirred for a further 16 h at 30 ° C and the solvent was added removed reduced pressure. To isolate the product, the reaction mixture was purified by HPLC.

Synthese von 2-(Pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin-5-aminSynthesis of 2- (pyridin-3-yl) [1,3] thiazolo [5,4-b] pyridin-5-amine Schritt 1: tert-Butyl-[2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin-5-yl]carbamat Step 1: tert -Butyl [2- (pyridin-3-yl) [1,3] thiazolo [5,4-b] pyridin-5-yl] carbamate

Figure imgb0281
Figure imgb0281

Unter einer Stickstoffatmosphäre wurde eine Mischung von 5-Brom-2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin (10,0 g, 34,2 mmol), tert-Butylcarbamat (6,63 g, 51,3 mmol), Cs2CO3 (33,46 g, 103,7 mmol), 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthen (3,96 g, 6,84 mmol) und Pd(OAc)2 (3,96 g, 6,85 mmol) in 1,4-Dioxan (100 mL) für 2 h auf 80 °C erhitzt. Das Lösungsmittel wurde anschließend unter reduziertem Druck entfernt. Der Rückstand wurde mit Wasser (100 mL) verdünnt und mit Ethylacetat (3x100 mL) extrahiert. Die vereinigten organischen Phasen wurden mit einer gesättigten Natriumchlorid-Lösung gewaschen, mit Natriumsulfat getrocknet und filtriert. Das Lösungsmittel wurde unter reduziertem Druck entfernt und der Rückstand mittels MPLC an Kieselgel chromatographisch aufgetrennt (Gradient: Ethylacetat/Cyclohexan 20:80 → 40:60). So konnten 7.00 g (63%) tert-Butyl-[2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin-5-yl]carbamat erhalten werden.
MS: m/z 328,9 [M+H+]Under a nitrogen atmosphere, a mixture of 5-bromo-2- (pyridin-3-yl) [1,3] thiazolo [5,4-b] pyridine (10.0 g, 34.2 mmol), tert-butyl carbamate ( 6.63 g, 51.3 mmol), Cs 2 CO 3 (33.46 g, 103.7 mmol), 4,5-bis (diphenylphosphino) -9,9-dimethylxanthene (3.96 g, 6.84 g) mmol) and Pd (OAc) 2 (3.96 g, 6.85 mmol) in 1,4-dioxane (100 mL) for 2 h at 80 ° C heated. The solvent was then removed under reduced pressure. The residue was diluted with water (100 mL) and extracted with ethyl acetate (3x100 mL). The combined organic phases were washed with a saturated sodium chloride solution, dried with sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was chromatographed on silica gel by MPLC (gradient: ethyl acetate / cyclohexane 20:80 → 40:60). There was thus obtained 7.00 g (63%) of tert-butyl [2- (pyridin-3-yl) [1,3] thiazolo [5,4-b] pyridin-5-yl] carbamate.
MS: m / z 328.9 [M + H + ]

Schritt 2: 2-(Pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin-5-amin Step 2: 2- (Pyridin-3-yl) [1,3] thiazolo [5,4-b] pyridin-5-amine

Figure imgb0282
Figure imgb0282

Zu einer Lösung von tert-Butyl-[2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin-5-yl]carbamat (7,00 g, 21,3 mmol) in CH2Cl2 (100 mL) wurde Trifluoressigsäure (25 mL) gegeben. Das Gemisch wurde für 6 h bei 30 °C gerührt und anschließend das Lösungsmittel unter reduziertem Druck entfernt. Der Rückstand (6,80 g) wurde ohne weitere Reinigung für die nächste Reaktion verwendet.To a solution of tert -butyl- [2- (pyridin-3-yl) [1,3] thiazolo [5,4-b] pyridin-5-yl] carbamate (7.00 g, 21.3 mmol) in CH 2 Cl 2 (100 mL) was added to trifluoroacetic acid (25 mL). The mixture was stirred for 6 h at 30 ° C and then the solvent was removed under reduced pressure. The residue (6.80 g) was used without further purification for the next reaction.

Allgemeine Vorschrift zur Synthese von Amiden des 2-(Pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin-5-aminsGeneral procedure for the synthesis of amides of 2- (pyridin-3-yl) [1,3] thiazolo [5,4-b] pyridin-5-amine

Figure imgb0283
Figure imgb0283

Eine Lösung von 2-(Pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin-5-amin (684 mg, 2,00 mmol) und der jeweiligen Säure (4,00 mmol) in Dichlormethan (5 mL) wurde mit 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimid (575 mg, 3,00 mmol) und N,N-Dimethylpyridin-4-amin (732 mg, 5,99 mmol) versetzt. Die Reaktionsmischung wurde für 16 h bei 30 °C gerührt und das Lösungsmittel unter reduziertem Druck entfernt. Der Rückstand wurde mit Wasser (10 mL) versetzt und mit Ethylacetat (3x10 mL) extrahiert. Die vereinigten organischen Phasen wurden mit einer gesättigten Natriumchlorid-Lösung gewaschen, mit Natriumsulfat getrocknet und filtriert. Das Lösungsmittel wurde unter reduziertem Druck entfernt und der Rückstand mittels MPLC an Kieselgel chromatographisch aufgetrennt (Gradient: Ethylacetat/Cyclohexan 30:70 → 60:40). So konnten die Amide des 2-(Pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin-5-amins erhalten werden.A solution of 2- (pyridin-3-yl) [1,3] thiazolo [5,4-b] pyridine-5-amine (684 mg, 2.00 mmol) and the respective acid (4.00 mmol) in Dichloromethane (5 mL) was added with 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide (575 mg, 3.00 mmol) and N, N-dimethylpyridin-4-amine (732 mg, 5.99 mmol). The reaction mixture was stirred for 16 h at 30 ° C and the solvent removed under reduced pressure. The residue was treated with water (10 mL) and extracted with ethyl acetate (3x10 mL). The combined organic phases were washed with a saturated sodium chloride solution, dried with sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was chromatographed on silica gel by MPLC (gradient: ethyl acetate / cyclohexane 30:70 → 60:40). Thus, the amides of 2- (pyridin-3-yl) [1,3] thiazolo [5,4-b] pyridin-5-amine could be obtained.

Allgemeine Vorschrift zur Methylierung von sekundären Amiden des 2-(Pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin-5-aminsGeneral procedure for the methylation of secondary amides of 2- (pyridin-3-yl) [1,3] thiazolo [5,4-b] pyridin-5-amine

Figure imgb0284
Figure imgb0284

Zu einer Lösung des jeweiligen Amids (200 mg, 1.0 Äq.) in Dimethylformamid (4 mL) wurde Natriumhydrid (1,1 Äq.) gegeben und die Mischung für 30 min bei 30 °C gerührt. Anschließend wurde Methyliodid (1,0 Äq.) zugesetzt und die Mischung für weitere 30 min bei 30 °C gerührt. Die Reaktionsmischung wurde mit einer gesättigen wässrigen Lösung von Ammoniumchlorid (1 mL) versetzt und das Lösungsmittel unter reduziertem Druck entfernt. Zur Isolation des Produkts wurde die Reaktionsmischung per HPLC gereinigt.To a solution of the respective amide (200 mg, 1.0 eq.) In dimethylformamide (4 mL) was added sodium hydride (1.1 eq.) And the mixture was stirred at 30 ° C for 30 min. Then, methyl iodide (1.0 eq.) Was added and the mixture was stirred at 30 ° C for a further 30 min. The reaction mixture was added with a saturated aqueous solution of ammonium chloride (1 mL), and the solvent was removed under reduced pressure. To isolate the product, the reaction mixture was purified by HPLC.

Allgemeine Vorschrift zur Oxidation von Phenyl-trifluormethylsulfiden zu PhenyltrifluormethylsulfoxidenGeneral procedure for the oxidation of phenyl trifluoromethylsulphides to phenyltrifluoromethylsulphoxides

Eine Lösung des Trifluormethylsulfids (1.0 Äq) und meta-Chlorperbenzoesäure (1.0 Äq) in CH2Cl2 (3 mL) wurde für 16 h bei 30 °C gerührt. Das Lösungsmittel wurde unter reduziertem Druck entfernt und der Rückstand mittels MPLC an Kieselgel chromatographisch aufgetrennt (Gradient: Methanol/CH2Cl2 0:100 → 5:95). Anschließend wurder erneut mittels HPLC gereinigt (Laufmittel enthält Ameisensäure).A solution of trifluoromethyl sulfide (1.0 eq) and meta- chloroperbenzoic acid (1.0 eq) in CH 2 Cl 2 (3 mL) was stirred for 16 h at 30 ° C. The solvent was removed under reduced pressure and the residue was chromatographed on silica gel by MPLC (gradient: methanol / CH 2 Cl 2 O: 100 → 5:95). Subsequently, it was again purified by HPLC (mobile phase containing formic acid).

Allgemeine Vorschrift zur Oxidation von Phenyl-trifluormethylsulfiden zu PhenyltrifluormethylsulfonenGeneral procedure for the oxidation of phenyl trifluoromethyl sulfides to phenyltrifluoromethylsulfones

Eine Lösung des Trifluormethylsulfids (1.0 Äq) und meta-Chlorperbenzoesäure (2.0 Äq) in CH2Cl2 (3 mL) wurde für 16 h bei 30 °C gerührt. Das Lösungsmittel wurde unter reduziertem Druck entfernt und der Rückstand mittels MPLC an Kieselgel chromatographisch aufgetrennt (Gradient: Methanol/CH2Cl2 0:100 → 5:95). Anschließend wurder erneut mittels HPLC gereinigt (Laufmittel enthält Ameisensäure).A solution of trifluoromethylsulfide (1.0 eq) and meta- chloroperbenzoic acid (2.0 eq) in CH 2 Cl 2 (3 mL) was stirred for 16 h at 30 ° C. The solvent was removed under reduced pressure and the residue was chromatographed on silica gel by MPLC (gradient: methanol / CH 2 Cl 2 O: 100 → 5:95). Subsequently, it was again purified by HPLC (mobile phase containing formic acid).

Beispiel 1: 5-[2-Fluor-4-methyl-5-(2,2,2-trifluorethylsulfanyl)phenyl]-2-(3-pyridyl)thiazol[5,4-b]pyridin Example 1: 5- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfanyl) phenyl] -2- (3-pyridyl) thiazolo [5,4-b] pyridine

Figure imgb0285
Figure imgb0285

In Anlehnung an eine Reaktionsvorschrift aus WO 2010/071819 wurden (7 mg, 6 µmol) Wasser (0,65 mL) und 1,2-Dimethoxyethan (2,65 mL) zu einer Mischung von 5-Chlor-2-(3-pyridyl)thiazolo[5,4-b]pyridin (50 mg, 0,20 mmol), [2-Fluor-4-methyl-5-(2,2,2-trifluorethylsulfanyl)phenyl]boronsäure (97 mg, 0,36 mmol), Natriumcarbonat (64 mg, 0,61 mmol) und Tetrakis(triphenylphosphin)palladium gegeben. Die Reaktionsmischung wurde mehrfach mit einem Argonstrom gespült und das Gefäß verschlossen. Das Gemisch wurde in einer CEM Discover Mikrowelle für 40 min auf 140 °C erhitzt und nach dem Abkühlen auf Raumtemperatur durch einen Tiefenfilter filtriert, welcher mit Ethylacetat gespült wurde. Die Reaktion wurde insgesamt zweimal durchgeführt und die Ansätze vor der Reinigung vereinigt. Nach dem Entfernen des Lösungsmittels unter reduziertem Druck wurde der Rückstand mittels MPLC an Kieselgel chromatographisch aufgetrennt (Gradient: Ethylacetat/Cyclohexan 0:100 → 30:70). So wurden 96 mg (96% Reinheit, 52% Ausbeute) 5-[2-Fluor-4-methyl-5-(2,2,2-trifluorethylsulfanyl)phenyl]-2-(3-pyridyl)thiazol[5,4-b]pyridin erhalten.
1H-NMR(400,0 MHz, d6-DMSO): δ = 9,336(9,6); 9,331(9,4); 9,330(9,2); 8,819(7,7); 8,815(8,5); 8,807(8,3); 8,803(8,5); 8,615(14,3); 8,593(16,0); 8,536(4,4); 8,532(5,7); 8,530(5,6); 8,526(4,5); 8,516(4,8); 8,512(5,8); 8,510(6,2); 8,506(4,6); 8,318(0,8); 8,208(9,7); 8,188(9,7); 8,040(6,9); 8,036(7,9); 8,018(7,2); 8,014(6,9); 7,685(5,6); 7,683(5,7); 7,673(5,4); 7,671(5,5); 7,665(5,4); 7,663(5,4); 7,653(5,3); 7,651(5,4); 7,423(8,2); 7,411(0,5); 7,392(8,1); 4,008(4,2); 3,982(13,4); 3,956(14,0); 3,930(4,8); 3,330(261,5); 2,682(0,7); 2,677(1,5); 2,673(2,1); 2,668(1,6); 2,664(0,8); 2,656(0,3); 2,526(5,6); 2,521(8,5); 2,512(114,8); 2,508(235,5); 2,504(315,5); 2,499(263,2); 2,420(1,4); 2,368(0,5); 2,335(1,8); 2,330(2,1); 2,326(1,6); 2,321(0,9); 1,990(0,6); 1,398(4,1); 0,146(2,5); 0,029(0,4); 0,008(19,6); 0,000(555,1); -0,009(21,4); -0,033(0,4); -0,150(2,6).Based on a reaction rule WO 2010/071819 (7 mg, 6 μmol) water (0.65 mL) and 1,2-dimethoxyethane (2.65 mL) were added to a mixture of 5-chloro-2- (3-pyridyl) thiazolo [5,4-b] pyridine (50 mg, 0.20 mmol), [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfanyl) phenyl] boronic acid (97 mg, 0.36 mmol), sodium carbonate (64 mg, 0 , 61 mmol) and tetrakis (triphenylphosphine) palladium. The reaction mixture was rinsed several times with an argon stream and the vessel was closed. The mixture was heated to 140 ° C in a CEM Discover microwave for 40 minutes and, after cooling to room temperature, filtered through a depth filter which was rinsed with ethyl acetate. The reaction was carried out twice in total and the mixtures were combined before purification. After removing the solvent under reduced pressure, the residue was chromatographed on silica gel by MPLC (gradient: ethyl acetate / cyclohexane 0: 100 → 30:70). Thus, 96 mg (96% purity, 52% yield) of 5- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfanyl) phenyl] -2- (3-pyridyl) thiazole [5.4 -b] pyridine.
1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.366 (9.6); 9,331 (9.4); 9,330 (9.2); 8.819 (7.7); 8.815 (8.5); 8,807 (8.3); 8.803 (8.5); 8,615 (14.3); 8,593 (16.0); 8,536 (4.4); 8.532 (5.7); 8,530 (5.6); 8,526 (4.5); 8,516 (4.8); 8,512 (5.8); 8.510 (6.2); 8,506 (4.6); 8,318 (0.8); 8,208 (9.7); 8,188 (9.7); 8,040 (6.9); 8,036 (7.9); 8,018 (7.2); 8,014 (6.9); 7,685 (5.6); 7,683 (5.7); 7,673 (5.4); 7,671 (5.5); 7,665 (5.4); 7,663 (5.4); 7,653 (5.3); 7,651 (5.4); 7,423 (8.2); 7,411 (0.5); 7,392 (8.1); 4,008 (4.2); 3,982 (13.4); 3,956 (14.0); 3,930 (4.8); 3.330 (261.5); 2,682 (0.7); 2,677 (1.5); 2,673 (2.1); 2,668 (1.6); 2,664 (0.8); 2,656 (0.3); 2,526 (5.6); 2,521 (8.5); 2.512 (114.8); 2,508 (235.5); 2.504 (315.5); 2.499 (263.2); 2,420 (1.4); 2,368 (0.5); 2,335 (1.8); 2,330 (2.1); 2,326 (1.6); 2,321 (0.9); 1,990 (0.6); 1,398 (4.1); 0.146 (2.5); 0.029 (0.4); 0.008 (19.6); 0.000 (555.1); -0.009 (21.4); -0.033 (0.4); -0.150 (2.6).

Beispiel 2: 5-[4-Methyl-3-(2,2,2-trifluorethylsulfanyl)phenyl]-2-(3-pyridyl)thiazolo[5,4-b]pyridin Example 2 : 5- [4-Methyl-3- (2,2,2-trifluoroethylsulfanyl) phenyl] -2- (3-pyridyl) thiazolo [5,4-b] pyridine

Figure imgb0286
Figure imgb0286

Die Herstellung des 5-[4-Methyl-3-(2,2,2-trifluorethylsulfanyl)phenyl]-2-(3-pyridyl)thiazolo[5,4-b]pyridins erfolgte in Analogie zur Synthese des 5-[2-Fluor-4-methyl-5-(2,2,2-trifluorethylsulfanyl)phenyl]-2-(3-pyridyl)thiazol[5,4-b]pyridins. Dabei wurden 5-Chlor-2-(3-pyridyl)thiazolo[5,4-b]pyridin (50 mg, 0,20 mmol), [4-Methyl-3-(2,2,2-trifluorethylsulfanyl)phenyl]boronsäure (91 mg, 0,36 mmol), Tetrakis(triphenylphosphin)-palladium (7 mg, 6 µmol) und Natriumcarbonat (64 mg, 0,61 mmol) eingesetzt. Die Reaktion wurde zweimal durchgeführt und die Ansätze vor der Reinigung vereinigt. So wurden 125 mg 5-[4-Methyl-3-(2,2,2-trifluorethylsulfanyl)phenyl]-2-(3-pyridyl)thiazolo[5,4-b]pyridin (94% Reinheit, 70% Ausbeute) erhalten.
1H-NMR(400,0 MHz, d6-DMSO): δ = 9,322(1,9); 8,808(1,4); 8,799(1,4); 8,591(4,3); 8,581(0,4); 8,569(5,1); 8,560(0,4); 8,516(1,3); 8,511(1,9); 8,507(1,4); 8,496(1,4); 8,491(2,0); 8,487(1,4); 8,317(0,5); 8,307(3,9); 8,301(7,3); 8,279(4,2); 8,070(2,2); 8,066(2,1); 8,050(2,2); 8,046(2,2); 7,677(1,7); 7,666(1,7); 7,658(1,6); 7,646(1,6); 7,456(3,0); 7,436(2,8); 4,156(1,3); 4,130(4,2); 4,104(4,4); 4,078(1,5); 3,331(95,2); 2,677(0,4); 2,673(0,6); 2,668(0,5); 2,526(1,4); 2,512(35,3); 2,508(70,8); 2,504(93,0); 2,499(68,9); 2,495(34,7); 2,455(16,0); 2,391(0,8); 2,340(0,4); 2,335(0,5); 2,330(0,7); 2,326(0,5); 1,397(3,2); 0,008(0,4); 0,000(11,3); -0,008(0,5).The preparation of 5- [4-methyl-3- (2,2,2-trifluoroethylsulfanyl) phenyl] -2- (3-pyridyl) thiazolo [5,4-b] pyridine was carried out analogously to the synthesis of the 5- [2 -fluoro-4-methyl-5- (2,2,2-trifluorethylsulfanyl) phenyl] -2- (3-pyridyl) thiazolo [5,4-b] pyridine. Thereby, 5-chloro-2- (3-pyridyl) thiazolo [5,4-b] pyridine (50 mg, 0.20 mmol), [4-methyl-3- (2,2,2-trifluoroethylsulfanyl) phenyl] boronic acid (91 mg, 0.36 mmol), tetrakis (triphenylphosphine) palladium (7 mg, 6 μmol) and sodium carbonate (64 mg, 0.61 mmol). The reaction was carried out twice and the batches combined before purification. Thus, 125 mg of 5- [4-methyl-3- (2,2,2-trifluoroethylsulfanyl) phenyl] -2- (3-pyridyl) thiazolo [5,4-b] pyridine (94% purity, 70% yield). receive.
1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.322 (1.9); 8.808 (1.4); 8.799 (1.4); 8,591 (4.3); 8,581 (0.4); 8.569 (5.1); 8,560 (0.4); 8,516 (1.3); 8,511 (1.9); 8.507 (1.4); 8,496 (1.4); 8,491 (2.0); 8,487 (1.4); 8,317 (0.5); 8,307 (3.9); 8.301 (7.3); 8,279 (4.2); 8,070 (2.2); 8,066 (2.1); 8,050 (2.2); 8,046 (2.2); 7,677 (1.7); 7,666 (1.7); 7,658 (1.6); 7,646 (1.6); 7,456 (3.0); 7,436 (2.8); 4,156 (1.3); 4,130 (4.2); 4,104 (4.4); 4,078 (1.5); 3,331 (95.2); 2,677 (0.4); 2,673 (0.6); 2,668 (0.5); 2,526 (1.4); 2,512 (35.3); 2,508 (70.8); 2,504 (93.0); 2,499 (68.9); 2,495 (34.7); 2.455 (16.0); 2,391 (0.8); 2,340 (0.4); 2,335 (0.5); 2,330 (0.7); 2,326 (0.5); 1,397 (3.2); 0.008 (0.4); 0,000 (11.3); -0.008 (0.5).

Beispiel 3: 5-[2-Fluor-4-methyl-5-(2,2,2-trifluorethylsulfinyl)phenyl]-2-(3-pyridyl)thiazolo[5,4-b]pyridin Example 3: 5- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -2- (3-pyridyl) thiazolo [5,4-b] pyridine

Figure imgb0287
Figure imgb0287

Meta-Chlorperbenzoesäure (70% Reinheit, 33 mg, 0,14 mmol) wurde bei 0 °C zu einer Lösung von 6-[2-Fluor-4-methyl-5-(2,2,2-trifluorethylsulfanyl)phenyl]-2-(3-pyridyl)thiazolo[5,4-b]pyridin (60 mg, 0,13 mmol) in CH2Cl2 (2.5 mL) gegeben. Das Reaktionsgemisch wurde für 2 h bei Raumtemperatur gerührt und anschließend mit gesättigter Natriumcarbonat-Lösung versetzt. Nach 15 min wurden die Phasen getrennt, die wässrige Phase mit CH2Cl2 extrahiert und die vereinigten organischen Phasen mit Natriumsulfat getrocknet. Das Lösungsmittel wurde unter reduziertem Druck entfernt. Das Rohprodukt wurde mit CH2Cl2 gewaschen, nach Trocknung wurden 30 mg (97% Reinheit, 48% Ausbeute) des 5-[2-Fluor-4-methyl-5-(2,2,2-trifluorethylsulfinyl)phenyl]-2-(3-pyridyl)thiazolo[5,4-b]pyridins erhalten.
1H-NMR(400,0 MHz, d6-DMSO): δ = 9,341(3,3); 9,336(3,3); 8,823(2,3); 8,820(2,6); 8,811(2,5); 8,808(2,6); 8,654(3,6); 8,633(4,0); 8,593(0,4); 8,581(3,0); 8,562(3,0); 8,535(2,0); 8,530(1,5); 8,519(1,5); 8,514(2,0); 8,510(1,5); 8,317(0,4); 8,126(2,1); 8,122(2,4); 8,104(2,1); 8,101(2,1); 7,687(1,8); 7,675(1,9); 7,667(1,8); 7,655(1,7); 7,526(2,5); 7,496(2,5); 5,757(2,9); 4,261(0,4); 4,251(0,6); 4,232(1,0); 4,224(1,7); 4,205(1,9); 4,197(1,9); 4,178(1,7); 4,169(1,0); 4,150(0,6); 4,141(0,4); 3,329(81,5); 2,672(1,0); 2,668(0,8); 2,507(113,6); 2,503(144,6); 2,499(114,9); 2,468(16,0); 2,429(0,4); 2,330(1,0); 0,000(17,6). Meta- chloroperbenzoic acid (70% pure, 33 mg, 0.14 mmol) was added to a solution of 6- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfanyl) phenyl] at 0 ° C. Add 2- (3-pyridyl) thiazolo [5,4-b] pyridine (60 mg, 0.13 mmol) in CH 2 Cl 2 (2.5 mL). The reaction mixture was stirred for 2 h at room temperature and then treated with saturated sodium carbonate solution. After 15 minutes, the phases were separated, the aqueous phase extracted with CH 2 Cl 2 and the combined organic phases dried with sodium sulfate. The solvent was removed under reduced pressure. The crude product was washed with CH 2 Cl 2 , after drying, 30 mg (97% purity, 48% yield) of 5- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] - 2- (3-pyridyl) thiazolo [5,4-b] pyridine.
1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.341 (3.3); 9,336 (3.3); 8.823 (2.3); 8,820 (2.6); 8,811 (2.5); 8.808 (2.6); 8,654 (3.6); 8.633 (4.0); 8,593 (0.4); 8,581 (3.0); 8.562 (3.0); 8,535 (2.0); 8,530 (1.5); 8,519 (1.5); 8,514 (2.0); 8.510 (1.5); 8,317 (0.4); 8,126 (2.1); 8,122 (2.4); 8,104 (2.1); 8,101 (2.1); 7,687 (1.8); 7,675 (1.9); 7,667 (1.8); 7.655 (1.7); 7,526 (2.5); 7,496 (2.5); 5,757 (2.9); 4,261 (0.4); 4,251 (0.6); 4,232 (1.0); 4,224 (1.7); 4,205 (1.9); 4,197 (1.9); 4,178 (1.7); 4,169 (1.0); 4,150 (0.6); 4,141 (0.4); 3,329 (81.5); 2,672 (1.0); 2,668 (0.8); 2.507 (113.6); 2.503 (144.6); 2.499 (114.9); 2,468 (16.0); 2,429 (0.4); 2,330 (1.0); 0,000 (17.6).

Beispiel 4: 5-[4-Methyl-3-(2,2,2-trifluorethylsulfinyl)phenyl]-2-(3-pyridyl)thiazolo[5,4-b]pyridin Example 4: 5- [4-Methyl-3- (2,2,2-trifluoroethylsulfinyl) phenyl] -2- (3-pyridyl) thiazolo [5,4-b] pyridine

Figure imgb0288
Figure imgb0288

Die Herstellung des 5-[4-Methyl-3-(2,2,2-trifluorethylsulfinyl)phenyl]-2-(3-pyridyl)thiazolo[5,4-b]pyridin erfolgte in Analogie zur Synthese des 5-[2-Fluor-4-methyl-5-(2,2,2-trifluorethylsulfinyl)phenyl]-2-(3-pyridyl)thiazolo[5,4-b]pyridis. Dabei wurden 5-[4-Methyl-3-(2,2,2-trifluorethylsulfanyl)phenyl]-2-(3-pyridyl)thiazolo[5,4-b]pyridin (88 mg, 0,20 mmol) und meta-Chlorperbenzoesäure (70% Reinheit, 50 mg, 0,20 mmol) eingesetzt. Es wurden 27 mg (92% Reinheit, 29% Ausbeute) des 5-[4-Methyl-3-(2,2,2-trifluorethylsulfinyl)phenyl]-2-(3-pyridyl)thiazolo[5,4-b]pyridins erhalten.
1H-NMR(400,0 MHz, d6-DMSO): δ = 9,325(3,3); 9,320(3,3); 8,813(2,4); 8,810(2,6); 8,802(2,5); 8,798(2,6); 8,717(4,0); 8,713(4,2); 8,629(3,7); 8,607(4,3); 8,522(1,4); 8,517(2,0); 8,512(1,5); 8,502(1,5); 8,497(2,1); 8,492(1,4); 8,338(2,3); 8,331(5,1); 8,318(2,6); 8,310(4,1); 7,680(1,8); 7,668(1,8); 7,660(1,8); 7,648(1,7); 7,552(2,9); 7,532(2,8); 5,758(0,9); 4,235(0,7); 4,226(0,7); 4,208(2,0); 4,199(1,9); 4,181(2,0); 4,172(2,0); 4,154(0,7); 4,145(0,7); 4,136(0,3); 3,366(0,3); 3,331(76,2); 2,672(0,7); 2,507(78,8); 2,503(100,7); 2,499(78,2); 2,460(16,0); 2,330(0,7); 0,000(2,6).The preparation of 5- [4-methyl-3- (2,2,2-trifluoroethylsulfinyl) phenyl] -2- (3-pyridyl) thiazolo [5,4-b] pyridine was carried out in analogy to the synthesis of the 5- [2 -fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -2- (3-pyridyl) thiazolo [5,4-b] pyridis. There was added 5- [4-methyl-3- (2,2,2-trifluoroethylsulfanyl) phenyl] -2- (3-pyridyl) thiazolo [5,4-b] pyridine (88 mg, 0.20 mmol) and meta - Chloroperbenzoic acid (70% purity, 50 mg, 0.20 mmol) used. There was added 27 mg (92% purity, 29% yield) of the 5- [4-methyl-3- (2,2,2-trifluoroethylsulfinyl) phenyl] -2- (3-pyridyl) thiazolo [5,4-b] received pyridines.
1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.325 (3.3); 9,320 (3.3); 8,813 (2.4); 8,810 (2.6); 8,802 (2.5); 8,798 (2.6); 8.717 (4.0); 8,713 (4.2); 8,629 (3.7); 8,607 (4.3); 8,522 (1.4); 8,517 (2.0); 8,512 (1.5); 8,502 (1.5); 8,497 (2.1); 8.492 (1.4); 8,338 (2.3); 8,331 (5.1); 8,318 (2.6); 8.310 (4.1); 7,680 (1.8); 7.668 (1.8); 7,660 (1.8); 7,648 (1.7); 7,552 (2.9); 7,532 (2.8); 5,758 (0.9); 4,235 (0.7); 4,226 (0.7); 4,208 (2.0); 4,199 (1.9); 4,181 (2.0); 4,172 (2.0); 4,154 (0.7); 4,145 (0.7); 4,136 (0.3); 3,366 (0.3); 3,331 (76.2); 2,672 (0.7); 2,507 (78.8); 2.503 (100.7); 2,499 (78.2); 2,460 (16.0); 2,330 (0.7); 0,000 (2.6).

Beispiel 6: 2-(3-Pyridyl)-5-pyrrolidin-1-yl-thiazolo[5,4-b]pyridin Example 6: 2- (3-Pyridyl) -5-pyrrolidin-1-yl-thiazolo [5,4-b] pyridine

Figure imgb0289
Figure imgb0289

Zu einer Lösung von 5-Chlor-2-(3-pyridyl)thiazolo[5,4-b]pyridin (100 mg, 0,40 mmol) in Dimethylformamid (3 mL) wurde Pyrrolidin (142 mg, 2 mmol) gegeben und die Reaktionsmischung für 4 h bei 100 °C gerührt. Nach Abkühlen auf Raumtemperatur wurden die Lösungsmittel unter reduziertem Druck entfernt und der verbleibende Rückstands mittels HPLC chromatographisch aufgetrennt. So konnten 36 mg (95% Reinheit, 32% Ausbeute) des 2-(3-Pyridyl)-5-pyrimidin-2-yl-thiazolo[5,4-b]pyridins erhalten werden.
1H-NMR(400,0 MHz, d6-DMSO): δ = 9,151(5,5); 9,147(5,6); 8,683(3,9); 8,679(4,2); 8,671(4,1); 8,667(4,1); 8,335(0,5); 8,327(2,5); 8,323(3,4); 8,318(2,6); 8,314(1,6); 8,307(2,7); 8,302(3,5); 8,298(2,5); 8,140(8,2); 8,118(8,6); 7,580(3,1); 7,569(3,1); 7,561(3,1); 7,549(2,9); 7,521(0,4); 6,731(7,9); 6,708(7,7); 5,754(1,8); 3,510(5,5); 3,494(14,2); 3,477(5,8); 3,316(134,8); 3,141(0,9); 2,675(1,7); 2,671(2,3); 2,666(1,7); 2,632(1,8); 2,571(0,4); 2,567(0,4); 2,562(0,4); 2,524(7,4); 2,510(135,4); 2,506(268,7); 2,502(352,7); 2,497(264,6); 2,493(136,1); 2,333(1,6); 2,328(2,2); 2,324(1,7); 2,018(0,7); 2,003(6,0); 1,993(7,0); 1,986(16,0); 1,980(7,3); 1,970(5,9); 1,335(0,8); 1,259(0,7); 1,250(0,6); 1,233(2,1); 0,854(0,4); 0,146(2,1); 0,031(0,4); 0,022(0,8); 0,008(17,8); 0,000(454,2); -0,008(23,0); -0,028(0,7);-0,150(2,2).To a solution of 5-chloro-2- (3-pyridyl) thiazolo [5,4-b] pyridine (100 mg, 0.40 mmol) in dimethylformamide (3 mL) was added pyrrolidine (142 mg, 2 mmol) and the reaction mixture stirred for 4 h at 100 ° C. After cooling to room temperature, the solvents were removed under reduced pressure and the remaining residue was chromatographed by HPLC. Thus, 36 mg (95% purity, 32% yield) of 2- (3-pyridyl) -5-pyrimidin-2-yl-thiazolo [5,4-b] pyridine was obtained.
1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.151 (5.5); 9,147 (5.6); 8,683 (3.9); 8,679 (4.2); 8,671 (4.1); 8,667 (4.1); 8,335 (0.5); 8,327 (2.5); 8.323 (3.4); 8,318 (2.6); 8.314 (1.6); 8,307 (2.7); 8,302 (3.5); 8,298 (2.5); 8,140 (8.2); 8,118 (8.6); 7,580 (3.1); 7,569 (3.1); 7,561 (3.1); 7,549 (2.9); 7.521 (0.4); 6,731 (7.9); 6,708 (7.7); 5,754 (1.8); 3,510 (5.5); 3,494 (14.2); 3,477 (5.8); 3.316 (134.8); 3,141 (0.9); 2,675 (1.7); 2,671 (2.3); 2,666 (1.7); 2,632 (1.8); 2,571 (0.4); 2,567 (0.4); 2,562 (0.4); 2,524 (7.4); 2,510 (135.4); 2.506 (268.7); 2.502 (352.7); 2.497 (264.6); 2,493 (136.1); 2,333 (1.6); 2,328 (2.2); 2,324 (1.7); 2,018 (0.7); 2,003 (6.0); 1,993 (7.0); 1,986 (16.0); 1,980 (7.3); 1,970 (5.9); 1.335 (0.8); 1,259 (0.7); 1,250 (0.6); 1,233 (2.1); 0.854 (0.4); 0.146 (2.1); 0.031 (0.4); 0.022 (0.8); 0.008 (17.8); 0.000 (454.2); -0.008 (23.0); -0.028 (0.7) - 0.150 (2.2).

Beispiel 7: 2-(3-Pyridyl)-5-pyrimidin-2-yl-thiazolo[5,4-b]pyridin Example 7: 2- (3-Pyridyl) -5-pyrimidin-2-yl-thiazolo [5,4-b] pyridine

Figure imgb0290
Figure imgb0290

In Anlehnung an die Reaktionsvorschrift aus WO 2013/159064 wurde unter Argon 1,4-Dioxan (2 mL) zu einer Mischung von 5-Chlor-2-(3-pyridyl)thiazolo[5,4-b]pyridin (100 mg, 0,40 mmol), 2-(Tributylstannyl)pyrimidin (0,16 mL, 0,50 mmol), Kupfer(I)-iodid (23 mg, 0,12 mmol) und Tetrakis(triphenylphosphin)palladium (51 mg, 44 µmol) gegeben. Die Reaktionsmischung wurde für 16 h bei 90 °C gerührt und nach dem Abkühlen auf Raumtemperatur das Lösungsmittel unter reduziertem Druck entfernt. Der Rückstand wurde mittels MPLC an Kieselgel chromatographisch aufgetrennt (Gradient: Ethylacetat/Cyclohexan 0:100 → 100:0). Das erhaltene Produkt wurde in THF (2 mL) gelöst und mit einer Lösung von Kaliumfluorid (116 mg, 200 µmol) in Wasser (2 mL) versetzt. Die Lösung wurde für 15 min bei Raumtemperatur gerührt und anschließend mit Ethylacetat extrahiert. Die vereinigten organischen Phasen wurden mit Na2SO4 getrocknet und das Lösungsmittel unter reduziertem Druck entfernt. Der Rückstand wurde über Kieselgel filtriert, wobei mit Ethylacetat und Methanol nachgespült wurde. So konnten 5 mg (100% Reinheit, 4% Ausbeute) des 2-(3-Pyridyl)-5-pyrimidin-2-yl-thiazolo[5,4-b]pyridins erhalten werden.
1H-NMR(400,0 MHz, d6-DMSO): δ = 9,357(3,1); 9,352(3,1); 9,049(8,9); 9,037(9,0); 8,829(2,3); 8,825(2,5); 8,817(2,4); 8,813(2,4); 8,667(16,0); 8,564(1,3); 8,560(1,9); 8,555(1,4); 8,544(1,4); 8,539(1,9); 8,535(1,3); 8,319(0,7); 7,690(1,7); 7,678(1,7); 7,671(1,7); 7,659(1,6); 7,634(2,5); 7,622(4,7); 7,610(2,4); 5,759(1,0); 3,330(115,0); 2,676(1,3); 2,672(1,7); 2,667(1,3); 2,525(4,6); 2,507(204,2); 2,503(264,8); 2,498(196,5); 2,334(1,3); 2,329(1,7); 2,325(1,3); 1,258(0,5); 1,233(1,9); 0,852(0,6); 0,833(0,3); 0,146(0,6); 0,008(4,5); 0,000(124,1); -0,150(0,6).Based on the reaction procedure WO 2013/159064 under argon, 1,4-dioxane (2 mL) was added to a mixture of 5-chloro-2- (3-pyridyl) thiazolo [5,4-b] pyridine (100 mg, 0.40 mmol), 2- (tributylstannyl ) pyrimidine (0.16 mL, 0.50 mmol), copper (I) iodide (23 mg, 0.12 mmol) and tetrakis (triphenylphosphine) palladium (51 mg, 44 μmol). The reaction mixture was stirred for 16 h at 90 ° C and after cooling to room temperature the solvent was removed under reduced pressure. The residue was chromatographed on silica gel by MPLC (gradient: ethyl acetate / cyclohexane 0: 100 → 100: 0). The resulting product was dissolved in THF (2 mL) and treated with a solution of potassium fluoride (116 mg, 200 .mu.mol) in water (2 mL). The solution was stirred for 15 min at room temperature and then extracted with ethyl acetate. The combined organic phases were dried with Na 2 SO 4 and the solvent removed under reduced pressure. The residue was filtered through silica gel, rinsing with ethyl acetate and methanol. Thus, 5 mg (100% purity, 4% yield) of 2- (3-pyridyl) -5-pyrimidin-2-yl-thiazolo [5,4-b] pyridine was obtained.
1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.357 (3.1); 9,352 (3.1); 9.049 (8.9); 9,037 (9.0); 8.829 (2.3); 8,825 (2.5); 8.817 (2.4); 8,813 (2.4); 8,667 (16.0); 8,564 (1.3); 8,560 (1.9); 8.555 (1.4); 8.544 (1.4); 8,539 (1.9); 8,535 (1.3); 8,319 (0.7); 7,690 (1.7); 7,678 (1.7); 7,671 (1.7); 7.659 (1.6); 7,634 (2.5); 7,622 (4.7); 7,610 (2.4); 5,759 (1.0); 3.330 (115.0); 2,676 (1.3); 2,672 (1.7); 2,667 (1.3); 2,525 (4.6); 2.507 (204.2); 2.503 (264.8); 2.498 (196.5); 2,334 (1.3); 2,329 (1.7); 2,325 (1.3); 1,258 (0.5); 1,233 (1.9); 0.852 (0.6); 0.833 (0.3); 0.146 (0.6); 0.008 (4.5); 0.000 (124.1); -0.150 (0.6).

Beispiel 8: 5-(2-Pyridyl)-2-(3-pyridyl)thiazolo[5,4-b]pyridin Example 8: 5- (2-Pyridyl) -2- (3-pyridyl) thiazolo [5,4-b] pyridine

Figure imgb0291
Figure imgb0291

In Anlehnung an die Reaktionsvorschrift aus Journal of Organic Chemistry (2010), 75, 8830 - 8832 wurde eine Lösung von 2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (15 mg, 31 µmol) und Tris(dibenzylidenaceton)dipalladium (7,4 mg, 8,1 µmol) in THF (2,3 mL) unter Argon für 10 min bei 65 °C gerührt. Anschließend wurde 5-Chlor-2-(3-pyridyl)thiazolo[5,4-b]pyridin (100 mg, 0,40 mmol) als Suspension in THF (3 mL) zugesetzt. Das Heizbad wurde entfernt und eine Lösung von 2-Pyridylzinkbromid in THF (0,5 M, 1,21 mL, 0,6 mmol) hinzugetropft. Das Reaktionsgemisch wurde für 2 h bei Raumtemperatur, 8 h bei 65 °C sowie weitere 62 h bei Raumtemperatur gerührt und anschließend mit einer halbgesättigen Lösung von NaHCO3 versetzt. Die Phasen wurden getrennt und die wässrige Phase mit Ethylacetat extrahiert. Die vereinigten organischen Phasen wurden mit Wasser gewaschen, mit Na2SO4 getrocknet und die Lösungsmittel unter reduziertem Druck entfernt. Der Rückstand wurde mittels MPLC an Kieselgel chromatographisch aufgetrennt (Gradient: Ethylacetat/Cyclohexan 0:100 → 70:30). So wurden 19 mg (100% Reinheit, 16% Ausbeute) des 5-(2-Pyridyl)-2-(3-pyridyl)thiazolo[5,4-b]pyridins erhalten.
1H-NMR(601,6 MHz, CDCl3): δ = 9,345(6,9); 9,344(7,1); 9,342(7,2); 9,341(6,4); 8,772(5,8); 8,769(5,9); 8,764(6,0); 8,762(5,7); 8,737(3,9); 8,736(4,6); 8,734(4,6); 8,733(4,0); 8,729(4,2); 8,728(4,6); 8,727(4,4); 8,725(3,6); 8,648(12,4); 8,634(14,1); 8,511(4,7); 8,510(6,8); 8,508(4,3); 8,498(4,9); 8,497(7,1); 8,495(4,3); 8,426(15,6); 8,422(5,2); 8,421(4,8); 8,418(3,8); 8,412(16,0); 8,409(5,6); 8,408(5,0); 8,405(3,7); 7,883(3,5); 7,880(3,4); 7,870(5,6); 7,868(5,5); 7,857(3,6); 7,854(3,4); 7,498(4,4); 7,496(4,2); 7,490(4,5); 7,488(4,3); 7,484(4,4); 7,483(4,1); 7,477(4,3); 7,475(4,0); 7,434(0,3); 7,369(3,9); 7,368(3,8); 7,362(3,9); 7,360(4,1); 7,357(4,1); 7,355(3,7); 7,349(3,7); 7,347(3,4); 7,262(58,9); 7,086(0,3); 1,594(59,7); 1,333(0,7); 1,284(1,0); 1,254(1,5); 0,880(0,3); 0,844(0,4); 0,839(0,4); 0,005(1,5); 0,000(45,7); -0,006(1,7).Based on the reaction procedure Journal of Organic Chemistry (2010), 75, 8830-8832 A solution of 2-dicyclohexylphosphino-2 ', 4', 6'-triisopropylbiphenyl (15 mg, 31 μmol) and tris (dibenzylideneacetone) dipalladium (7.4 mg, 8.1 μmol) in THF (2.3 mL) was added. stirred under argon at 65 ° C for 10 min. Then 5-chloro-2- (3-pyridyl) thiazolo [5,4-b] pyridine (100 mg, 0.40 mmol) was added as a suspension in THF (3 mL). The heating bath was removed and a solution of 2-pyridylzinc bromide in THF (0.5 M, 1.21 mL, 0.6 mmol) was added dropwise. The reaction mixture was stirred for 2 h at room temperature, 8 h at 65 ° C and a further 62 h at room temperature and then treated with a half-saturated solution of NaHCO 3 . The phases were separated and the aqueous phase extracted with ethyl acetate. The combined organic phases were washed with water, dried with Na 2 SO 4 and the solvents removed under reduced pressure. The residue was chromatographed on silica gel by MPLC (gradient: ethyl acetate / cyclohexane 0: 100 → 70:30). Thus, 19 mg (100% purity, 16% yield) of 5- (2-pyridyl) -2- (3-pyridyl) thiazolo [5,4-b] pyridine was obtained.
1 H-NMR (601.6 MHz, CDCl 3): δ = 9.345 (6.9); 9,344 (7.1); 9,342 (7.2); 9,341 (6.4); 8.772 (5.8); 8.769 (5.9); 8.764 (6.0); 8.762 (5.7); 8,737 (3.9); 8,736 (4.6); 8,734 (4.6); 8,733 (4.0); 8,729 (4.2); 8,728 (4.6); 8,727 (4.4); 8,725 (3.6); 8.648 (12.4); 8,634 (14.1); 8,511 (4.7); 8.510 (6.8); 8,508 (4.3); 8,498 (4.9); 8,497 (7.1); 8,495 (4.3); 8,426 (15.6); 8,422 (5.2); 8,421 (4.8); 8,418 (3.8); 8.412 (16.0); 8,409 (5.6); 8.408 (5.0); 8.405 (3.7); 7,883 (3.5); 7,880 (3.4); 7,870 (5.6); 7,868 (5.5); 7,857 (3.6); 7,854 (3.4); 7,498 (4.4); 7,496 (4.2); 7,490 (4.5); 7,488 (4.3); 7,484 (4.4); 7,483 (4.1); 7,477 (4.3); 7,475 (4.0); 7,434 (0.3); 7,369 (3.9); 7,368 (3.8); 7,362 (3.9); 7,360 (4.1); 7,357 (4.1); 7,355 (3.7); 7,349 (3.7); 7,347 (3.4); 7,262 (58.9); 7,086 (0.3); 1.594 (59.7); 1.333 (0.7); 1,284 (1.0); 1,254 (1.5); 0.880 (0.3); 0.844 (0.4); 0.839 (0.4); 0.005 (1.5); 0,000 (45.7); -0.006 (1.7).

Beispiel 9: N-[4-Methyl-3-(2,2,2-trifluorethylsulfanyl)phenyl]-2-(3-pyridyl)thiazolo[5,4-b]pyridin-5-amin Example 9: N - [4-Methyl-3- (2,2,2-trifluoroethylsulfanyl) phenyl] -2- (3-pyridyl) thiazolo [5,4-b] pyridin-5-amine

Figure imgb0292
Figure imgb0292

Die Herstellung des N-[4-Methyl-3-(2,2,2-trifluorethylsulfanyl)phenyl]-2-(3-pyridyl)thiazolo[5,4-b]pyridin-5-amins erfolgte in Analogie zur Synthese des 4-[2-(3-Pyridyl)thiazolo[5,4-b]pyridin-5-yl]morpholins. Dabei wurden 5-Chlor-2-(3-pyridyl)thiazolo[5,4-b]pyridin (100 mg, 0,40 mmol), 4-Methyl-3-(2,2,2-trifluorethylsulfanyl)aniline (134 mg, 0,61 mmol), Palladium(II)acetat (4,5 mg, 20 µmol), rac-(2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl) (5 mg, 8 µmol) und Natrium-tert-butanolat (58 mg, 0,60 mmol) eingesetzt. Es wurden 72 mg (94% Reinheit, 38% Ausbeute) des N-[4-Methyl-3-(2,2,2-trifluorethylsulfanyl)phenyl]-2-(3-pyridyl)thiazolo[5,4-b]pyridin-5-amins erhalten.
1H-NMR(400,0 MHz, d6-DMSO): δ = 9,638(3,9); 9,195(2,9); 9,191(3,0); 8,717(2,3); 8,713(2,4); 8,705(2,4); 8,701(2,4); 8,378(1,2); 8,374(1,7); 8,368(1,3); 8,358(1,4); 8,353(1,8); 8,348(1,4); 8,318(0,4); 8,236(4,2); 8,214(4,5); 8,007(3,2); 8,002(3,3); 7,607(1,7); 7,595(1,6); 7,587(1,6); 7,573(2,1); 7,571(2,0); 7,565(1,7); 7,550(2,0); 7,545(2,0); 7,236(2,9); 7,215(2,5); 7,038(4,0); 7,015(4,0); 4,056(0,4); 4,038(1,1); 4,020(1,1); 4,002(0,4); 3,954(1,2); 3,928(3,7); 3,902(3,9); 3,876(1,3); 3,330(134,6); 2,676(0,8); 2,672(1,1); 2,667(0,8); 2,525(3,4); 2,511(66,4); 2,507(131,9); 2,503(172,2); 2,498(126,1); 2,494(63,2); 2,338(16,0); 2,266(0,5); 1,989(4,8); 1,397(0,4); 1,193(1,3); 1,175(2,5); 1,157(1,3); 0,146(0,9); 0,008(7,6); 0,000(197,5); -0,008(8,7); -0,150(0,9).The preparation of N - [4-methyl-3- (2,2,2-trifluoroethylsulfanyl) phenyl] -2- (3-pyridyl) thiazolo [5,4-b] pyridine-5-amine was carried out analogously to the synthesis of 4- [2- (3-pyridyl) thiazolo [5,4-b] pyridin-5-yl] morpholine. Thereby, 5-chloro-2- (3-pyridyl) thiazolo [5,4-b] pyridine (100 mg, 0.40 mmol), 4-methyl-3- (2,2,2-trifluoroethylsulfanyl) aniline (134 mg, 0.61 mmol), palladium (II) acetate (4.5 mg, 20 μmol), rac - (2,2'-bis (diphenylphosphino) -1,1'-binaphthyl) (5 mg, 8 μmol) and sodium tert-butoxide (58 mg, 0.60 mmol). There was added 72 mg (94% purity, 38% yield) of N - [4-methyl-3- (2,2,2-trifluoroethylsulfanyl) phenyl] -2- (3-pyridyl) thiazolo [5,4-b] pyridine-5-amine obtained.
1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.638 (3.9); 9,195 (2.9); 9.191 (3.0); 8.717 (2.3); 8,713 (2.4); 8.705 (2.4); 8.701 (2.4); 8,378 (1.2); 8,374 (1.7); 8,368 (1.3); 8,358 (1.4); 8,353 (1.8); 8.348 (1.4); 8,318 (0.4); 8,236 (4.2); 8,214 (4.5); 8,007 (3.2); 8.002 (3.3); 7,607 (1.7); 7,595 (1.6); 7,587 (1.6); 7.573 (2.1); 7,571 (2.0); 7,565 (1.7); 7,550 (2.0); 7,545 (2.0); 7,236 (2.9); 7.215 (2.5); 7,038 (4.0); 7.015 (4.0); 4,056 (0.4); 4,038 (1.1); 4,020 (1.1); 4,002 (0.4); 3,954 (1.2); 3,928 (3.7); 3,902 (3.9); 3,876 (1.3); 3.330 (134.6); 2,676 (0.8); 2,672 (1.1); 2,667 (0.8); 2,525 (3.4); 2,511 (66.4); 2.507 (131.9); 2.503 (172.2); 2.498 (126.1); 2,494 (63.2); 2,338 (16.0); 2,266 (0.5); 1,989 (4.8); 1,397 (0.4); 1.193 (1.3); 1.175 (2.5); 1,157 (1.3); 0.146 (0.9); 0.008 (7.6); 0.000 (197.5); -0.008 (8.7); -0.150 (0.9).

Beispiel 11: 4-[2-(3-Pyridyl)thiazolo[5,4-b]pyridin-5-yl]morpholin Example 11: 4- [2- (3-Pyridyl) thiazolo [5,4-b] pyridin-5-yl] morpholine

Figure imgb0293
Figure imgb0293

In Anlehnung an die Reaktionsvorschrift aus WO 2007/148093 wurde Toluol (0,75 mL) zu einer Mischung von 5-Chlor-2-(3-pyridyl)thiazolo[5,4-b]pyridin (100 mg, 0,40 mmol), Morpholin (53 µL, 0,61 mmol), Palladium(II)acetat (4,5 mg, 20 µmol), rac-(2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl) (5 mg, 8 µmol) und Natrium-tert-butanolat (58 mg, 0,60 mmol) gegeben. Die Reaktionsmischung wurde durch 20 minütiges Einleiten eines Argonstroms von gelöstem Sauerstoff befreit und anschließend für 16 h bei 110 °C gerührt. Nach dem Abkühlen auf Raumtemperatur wurde die Mischung durch einen Tiefenfilter filtriert, welcher anschließend mit Ethylacetat gespült wurde. Das Lösungsmittel wurde unter reduziertem Druck entfernt und der Rückstand mittels MPLC an Kieselgel chromatographisch aufgetrennt (Gradient: Ethylacetat/Cyclohexan 0:100 → 100:0). So konnten 29 mg (100% Reinheit, 24% Ausbeute) des 4-[2-(3-Pyridyl)thiazolo[5,4-b]pyridin-5-yl]morpholins erhalten werden.
1H-NMR(400,0 MHz, d6-DMSO): δ = 9,179(5,8); 9,174(5,8); 8,709(4,1); 8,706(4,4); 8,697(4,3); 8,694(4,2); 8,356(3,6); 8,336(3,7); 8,317(0,4); 8,222(6,4); 8,199(6,7); 7,598(3,3); 7,586(3,4); 7,578(3,3); 7,566(3,0); 7,138(6,3); 7,115(6,1); 3,745(9,6); 3,733(16,0); 3,721(13,6); 3,609(13,4); 3,596(15,7); 3,585(9,5); 3,332(188,8); 2,672(1,2); 2,503(168,0); 2,330(1,1); 1,990(0,5); 0,000(15,6).Based on the reaction procedure WO 2007/148093 Toluene (0.75 mL) was added to a mixture of 5-chloro-2- (3-pyridyl) thiazolo [5,4-b] pyridine (100 mg, 0.40 mmol), morpholine (53 μL, 0.61 mmol), palladium (II) acetate (4.5 mg, 20 .mu.mol), rac - (2,2'-bis (diphenylphosphino) -1,1'-binaphthyl) (5 mg, 8 .mu.mol) and sodium tert. butanolate (58 mg, 0.60 mmol). The reaction mixture was freed from dissolved oxygen by introducing an argon stream for 20 minutes and then stirred at 110 ° C. for 16 hours. After cooling to room temperature, the mixture was filtered through a depth filter, which was then rinsed with ethyl acetate. The solvent was removed under reduced pressure and the residue was chromatographed on silica gel by MPLC (gradient: ethyl acetate / cyclohexane 0: 100 → 100: 0). Thus, 29 mg (100% purity, 24% yield) of 4- [2- (3-pyridyl) thiazolo [5,4-b] pyridin-5-yl] morpholine could be obtained.
1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.179 (5.8); 9,174 (5.8); 8,709 (4.1); 8,706 (4.4); 8.697 (4.3); 8.694 (4.2); 8.356 (3.6); 8,336 (3.7); 8,317 (0.4); 8.222 (6.4); 8,199 (6.7); 7.598 (3.3); 7,586 (3.4); 7,578 (3.3); 7,566 (3.0); 7,138 (6.3); 7,115 (6.1); 3,745 (9.6); 3,733 (16.0); 3,721 (13.6); 3,609 (13.4); 3,596 (15.7); 3,585 (9.5); 3.332 (188.8); 2,672 (1.2); 2.503 (168.0); 2,330 (1.1); 1,990 (0.5); 0,000 (15.6).

Beispiel 12: N-Methyl-N-[4-methyl-3-(2,2,2-trifluorethylsulfanyl)phenyl]-2-(3-pyridyl)thiazolo[5,4-b]pyridin-5-amin Example 12: N-methyl-N- [4-methyl-3- (2,2,2-trifluorethylsulfanyl) phenyl] -2- (3-pyridyl) thiazolo [5,4-b] pyridin-5-amine

Figure imgb0294
Figure imgb0294

Zu einer Lösung von N-[4-Methyl-3-(2,2,2-trifluorethylsulfanyl]-2-(3-pyridyl)thiazolo[5,4-b]pyridin-5-amin (59 mg, 0,12 mmol) in Tetrahydrofuran (1,2 mL) wurde bei 0 °C Natriumhydrid (7,6 mg, 0,19 mmol) gegeben und die Reaktionslösung für 15 min bei 0 °C gerührt. Es wurde Mehyliodid (16 µL, 0,25 mmol) hinzugefügt und das Reaktionsgemisch über Nacht bei Raumtemperatur gerührt. Anschließend wurde das Reaktionsgemisch erneut auf 0 °C abgekühlt, mit Natriumhydrid (5 mg, 0,2 mmol) und Methyliodid (8 µL, 0,13 mmol) versetzt und über Nacht bei Raumtemperatur gerührt. Zur Aufarbeitung wurde das Reaktionsgemisch mit einer gesättigten wässrigen Ammoniumchloridlösung versetzt, die Phasen getrennt und die wässrige Phase mehrmals mit Essigsäureethylester extrahiert. Die vereinigten organischen Phasen wurde mit Natriumsulfat getrocknet und die Lösungsmittel unter reduziertem Druck entfernt. Das Rohprodukt wurde mittels HPLC (Gradient: H2O/Acetonitril) chromatographisch aufgetrennt. So wurden 4,8 mg (94% Reinheit, 8% Ausbeute) des N-Methyl-N-[4-methyl-3-(2,2,2-trifluorethylsulfanyl)phenyl]-2-(3-pyridyl)thiazolo[5,4-b]pyridin-5-amins erhalten.
1H-NMR(601,6 MHz, CDCl3): δ = 9,227(1,6); 9,224(1,6); 8,677(1,1); 8,674(1,2); 8,669(1,2); 8,666(1,1); 8,297(0,8); 8,293(1,1); 8,290(0,8); 8,283(0,8); 8,280(1,1); 8,277(0,8); 7,901(2,9); 7,885(2,9); 7,424(1,0); 7,423(1,0); 7,413(2,4); 7,410(2,9); 7,403(1,0); 7,402(0,9); 7,310(1,5); 7,296(1,8); 7,264(3,3); 7,164(1,4); 7,160(1,3); 7,151(1,1); 7,147(1,1); 6,627(2,9); 6,611(2,9); 5,299(2,2); 3,545(1,4); 3,538(16,0); 3,438(1,1); 3,422(3,4); 3,406(3,5); 3,391(1,2); 2,491(10,7); 2,442(1,0); 2,359(0,7); 1,688(1,5); 1,254(1,6); 0,000(0,9).To a solution of N - [4-methyl-3- (2,2,2-trifluoroethylsulfanyl] -2- (3-pyridyl) thiazolo [5,4-b] pyridin-5-amine (59 mg, 0.12 mmol) in tetrahydrofuran (1.2 mL) was added sodium hydride (7.6 mg, 0.19 mmol) at 0 ° C. and the reaction solution was stirred for 15 min at 0 ° C. Myl iodide (16 μL, 0.25 The reaction mixture was again cooled to 0 ° C, treated with sodium hydride (5 mg, 0.2 mmol) and methyl iodide (8 μL, 0.13 mmol) and overnight For work-up, a saturated aqueous ammonium chloride solution was added to the reaction mixture, the phases were separated and the aqueous phase was extracted several times with ethyl acetate The combined organic phases were dried with sodium sulfate and the solvents were removed under reduced pressure The crude product was purified by HPLC (gradient : H 2 O / acetonitrile) chromatographically Thus, 4.8 mg (94% purity, 8% yield) of N -methyl-N- [4-methyl-3- (2,2,2-trifluoroethylsulfanyl) phenyl] -2- (3-pyridyl) was added. thiazolo [5,4-b] pyridine-5-amine.
1 H-NMR (601.6 MHz, CDCl 3): δ = 9.227 (1.6); 9,224 (1.6); 8.677 (1.1); 8.674 (1.2); 8,669 (1.2); 8,666 (1.1); 8,297 (0.8); 8.293 (1.1); 8,290 (0.8); 8,283 (0.8); 8,280 (1.1); 8,277 (0.8); 7.901 (2.9); 7,885 (2.9); 7,424 (1.0); 7,423 (1.0); 7,413 (2.4); 7.410 (2.9); 7,403 (1.0); 7,402 (0.9); 7.310 (1.5); 7,296 (1.8); 7,264 (3.3); 7,164 (1.4); 7,160 (1.3); 7,151 (1.1); 7,147 (1.1); 6,627 (2.9); 6,611 (2.9); 5,299 (2.2); 3,545 (1.4); 3,538 (16.0); 3,438 (1.1); 3,422 (3.4); 3,406 (3.5); 3,391 (1.2); 2,491 (10.7); 2,442 (1.0); 2,359 (0.7); 1,688 (1.5); 1,254 (1.6); 0.000 (0.9).

Beispiel 13: 2-(3-Pyridyl)-5-[4-(trifluormethyl)pyrazol-1-yl]thiazolo[5,4-b]pyridin Example 13: 2- (3-Pyridyl) -5- [4- (trifluoromethyl) pyrazol-1-yl] thiazolo [5,4-b] pyridine

Figure imgb0295
Figure imgb0295

In Anlehnung an die Reaktionsvorschrift aus Journal of Organic Chemistry (2004), 69, 5578-5587 wurden unter Argon 5-Chlor-2-(3-pyridyl)thiazolo[5,4-b]pyridin (100 mg, 0,40 mmol), trans-N,N'-Dimethylcyclohexan-1,2-diamin (22 µL, 0,14 mmol) und entgastes Toluol (1 mL) zu einer Mischung von Kupfer(I)-iodid (13 mg, 68 µmol), 4-(Trifluormethyl)-1H-pyrazol (46 mg, 0,34 mmol) und Kaliumcarbonat (98 mg, 0,71 mmol) gegeben. Das Gefäß wurde verschlossen und die Reaktionsmischung in einer CEM Discover Mikrowelle für 18 h auf 120 °C erhitzt. Nach dem Abkühlen auf Raumtemperatur wurde Ethylacetat zugegeben und die Mischung durch einen Tiefenfilter filtriert, welcher anschließend mit Ethylacetat gespült wurde. Das Lösungsmittel wurde unter reduziertem Druck entfernt und der Rückstand mittels MPLC an Kieselgel chromatographisch aufgetrennt (Gradient: Ethylacetat/Cyclohexan 0:100 → 50:50). Anschließend wurde erneut mittels HPLC (Gradient: H2O/Acetonitril) chromatographisch aufgetrennt. So wurden 10 mg (100% Reinheit, 9% Ausbeute) des 2-(3-Pyridyl)-5-[4-(trifluormethyl)pyrazol-1-yl]thiazolo[5,4-b]pyridins erhalten.
1H-NMR(400,0 MHz, d6-DMSO): δ = 9,397(12,4); 9,334(8,8); 9,330(8,9); 8,819(6,7); 8,816(7,5); 8,807(7,2); 8,804(7,4); 8,747(14,6); 8,725(16,0); 8,538(3,9); 8,533(5,4); 8,528(4,1); 8,518(4,3); 8,512(5,7); 8,508(4,3); 8,382(15,9); 8,317(2,8); 8,235(15,5); 8,213(14,5); 7,992(0,5); 7,684(5,1); 7,682(5,3); 7,672(4,9); 7,670(5,1); 7,664(4,9); 7,662(5,0); 7,652(4,7); 7,650(4,8); 3,329(899,6); 2,676(4,4); 2,672(6,1); 2,667(4,6); 2,542(2,4); 2,525(16,4); 2,520(24,9); 2,511(334,7); 2,507(693,8); 2,503(925,4); 2,498(682,8); 2,494(341,5); 2,334(4,3); 2,329(6,0); 2,325(4,5); 2,075(0,3); 1,148(0,6); 0,146(7,1); 0,032(1,0); 0,025(2,1); 0,008(54,7); 0,000(1562,0); -0,009(65,0); -0,029(1,5); -0,038(0,8);-0,042(0,6); -0,050(0,5); -0,065(0,4); -0,150(7,1).Based on the reaction procedure Journal of Organic Chemistry (2004), 69, 5578-5587 under argon, 5-chloro-2- (3-pyridyl) thiazolo [5,4-b] pyridine (100 mg, 0.40 mmol), trans -N, N'- dimethylcyclohexane-1,2-diamine (22 μL , 0.14 mmol) and degassed toluene (1 mL) to a mixture of copper (I) iodide (13 mg, 68 μmol), 4- (trifluoromethyl) -1H-pyrazole (46 mg, 0.34 mmol) and Potassium carbonate (98 mg, 0.71 mmol) was added. The vessel was capped and the reaction mixture heated in a CEM Discover microwave to 120 ° C for 18 h. After cooling to room temperature, ethyl acetate was added and the mixture was filtered through a depth filter, which was then rinsed with ethyl acetate. The solvent was removed under reduced pressure and the residue was chromatographed on silica gel by MPLC (gradient: ethyl acetate / cyclohexane 0: 100 → 50:50). Subsequently, again by HPLC (gradient: H 2 O / acetonitrile) was separated by chromatography. There was thus obtained 10 mg (100% purity, 9% yield) of 2- (3-pyridyl) -5- [4- (trifluoromethyl) pyrazol-1-yl] thiazolo [5,4-b] pyridine.
1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.397 (12.4); 9,334 (8.8); 9,330 (8.9); 8.819 (6.7); 8,816 (7.5); 8,807 (7.2); 8.804 (7.4); 8,747 (14.6); 8,725 (16.0); 8,538 (3.9); 8,533 (5.4); 8.528 (4.1); 8.518 (4.3); 8,512 (5.7); 8,508 (4.3); 8.382 (15.9); 8,317 (2.8); 8,235 (15.5); 8,213 (14.5); 7,992 (0.5); 7,684 (5.1); 7,682 (5.3); 7,672 (4.9); 7,670 (5.1); 7.664 (4.9); 7,662 (5.0); 7,652 (4.7); 7,650 (4.8); 3,329 (899.6); 2,676 (4.4); 2,672 (6.1); 2,667 (4.6); 2,542 (2.4); 2.525 (16.4); 2,520 (24.9); 2,511 (334.7); 2.507 (693.8); 2.503 (925.4); 2.498 (682.8); 2.494 (341.5); 2,334 (4.3); 2,329 (6.0); 2,325 (4.5); 2,075 (0.3); 1,148 (0.6); 0.146 (7.1); 0.032 (1.0); 0.025 (2.1); 0.008 (54.7); 0.000 (1562.0); -0.009 (65.0); -0.029 (1.5); -0.038 (0.8) - 0.042 (0.6); -0.050 (0.5); -0.065 (0.4); -0.150 (7.1).

Beispiel 14: N-Cyclopropyl-2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin-5-amin Example 14: N- Cyclopropyl-2- (pyridin-3-yl) [1,3] thiazolo [5,4-b] pyridin-5-amine

Figure imgb0296
Figure imgb0296

Zu einer Lösung von 5-Chlor-2-(3-pyridyl)thiazolo[5,4-b]pyridin (100 mg, 0,40 mmol) in Dimethylsulfoxid (3 mL) wurde Cyclopropylamin (0,28 mL, 4 mmol) gegeben und die Reaktionsmischung in einer Mikrowelle für 1,5 h auf 150 °C erhitzt. Nach Abkühlen auf Raumtemperatur wurden die Lösungsmittel unter reduziertem Druck entfernt und der verbleibende Rückstand mittels HPLC chromatographisch aufgetrennt. So konnten 12 mg (99% Reinheit, 11% Ausbeute) des N-Cyclopropyl-2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin-5-amins erhalten werden.
1H-NMR(400MHz, CDCl3): δ = 9,23 (s, 1 H), 8,68 - 8,67 (m, 1 H), 8,29 - 8,26 (m, 1 H), 8,12 - 8,09 (m, 1 H), 7,43 - 7,40 (m, 1 H), 6,96 - 6,94 (m, 1 H), 5,25 (s, 1 H), 2,66 - 2,62 (m, 1 H), 0,89 - 0,86 (m, 2 H), 0,65 - 0,63 (m, 2 H).To a solution of 5-chloro-2- (3-pyridyl) thiazolo [5,4-b] pyridine (100 mg, 0.40 mmol) in dimethyl sulfoxide (3 mL) was added cyclopropylamine (0.28 mL, 4 mmol). and the reaction mixture in a microwave for 1.5 h at 150 ° C heated. After cooling to room temperature, the solvents were removed under reduced pressure and the remaining residue was chromatographed by HPLC. Thus, 12 mg (99% purity, 11% yield) of N-cyclopropyl-2- (pyridin-3-yl) [1,3] thiazolo [5,4-b] pyridine-5-amine could be obtained.
1 H-NMR (400MHz, CDCl 3): δ = 9.23 (s, 1 H), 8.68 to 8.67 (m, 1 H), 8.29 to 8.26 (m, 1 H) , 8.12-8.09 (m, 1H), 7.43-7.40 (m, 1H), 6.96-6.94 (m, 1H), 5.25 (s, 1 H), 2.66 - 2.62 (m, 1H), 0.89 - 0.86 (m, 2H), 0.65 - 0.63 (m, 2H).

Beispiel 16: N-Methyl-N-[2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin-5-yl]cyclopropancarboxamid Example 16: N -Methyl- N - [2- (pyridin-3-yl) [1,3] thiazolo [5,4-b] pyridin-5-yl] cyclopropanecarboxamide

Figure imgb0297
Figure imgb0297

Zu einer Lösung von N-Methyl-2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin-5-amin (97 mg, 0,40 mmol) und Triethylamin (0,12 g, 1,2 mmol) in CH2Cl2 (4 mL) wurde bei 0 °C Cyclopropancarbonylchlorid (0,13 g, 1,2 mmol) gegeben und die Reaktionsmischung für 6 h bei 25 °C gerührt. Die Lösungsmittel wurden unter reduziertem Druck entfernt und der verbleibende Rückstand mittels HPLC chromatographisch aufgetrennt. So konnten 64 mg (99% Reinheit, 52% Ausbeute) des N-Methyl-N-[2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin-5-yl]cyclopropancarboxamids erhalten werden.
1H-NMR(400MHz, CDCl3): δ = 9,13 (s, 1 H), 8,77 - 8,76 (m, 1 H), 8,38 - 8,31 (m, 2 H), 7,59 - 7,57 (m, 1 H), 7,50 - 7,47 (m, 1 H), 3,54 (s, 3 H), 1,73 - 1,70 (m, 1 H), 1,18 - 1,14 (m, 2 H), 0,84 - 0,80 (m, 2 H).To a solution of N-methyl-2- (pyridin-3-yl) [1,3] thiazolo [5,4-b] pyridin-5-amine (97 mg, 0.40 mmol) and triethylamine (0.12 g, 1.2 mmol) in CH 2 Cl 2 (4 mL) was added cyclopropanecarbonyl chloride (0.13 g, 1.2 mmol) at 0 ° C and the reaction mixture stirred at 25 ° C for 6 h. The solvents were removed under reduced pressure and the remaining residue was chromatographed by HPLC. Thus, 64 mg (99% purity, 52% yield) of the N- methyl- N - [2- (pyridin-3-yl) [1,3] thiazolo [5,4-b] pyridin-5-yl] cyclopropanecarboxamide to be obtained.
1 H-NMR (400MHz, CDCl 3): δ = 9.13 (s, 1 H), 8.77 to 8.76 (m, 1 H), 8.38 to 8.31 (m, 2 H) , 7.59 - 7.57 (m, 1H), 7.50 - 7.47 (m, 1H), 3.54 (s, 3H), 1.73 - 1.70 (m, 1 H), 1.18-1.14 (m, 2H), 0.84-0.80 (m, 2H).

Beispiel 17: N-Ethyl-N-[2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin-5-yl]methansulfonamid Example 17: N -Ethyl-N- [2- (pyridin-3-yl) [1,3] thiazolo [5,4-b] pyridin-5-yl] methanesulfonamide

Figure imgb0298
Figure imgb0298

Zu einer Lösung von N-Ethyl-2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin-5-amin (103 mg, 0,40 mmol) in THF (4 mL) wurde bei -20 °C Lithiumhexamethyldisilazid (1,2 mL, 1,2 mmol, 1M in THF) gegeben und die Reaktionsmischung für 10 min gerührt. Anschließend wurde Methansulfonylchlorid (0,14 g, 1,2 mmol) hinzugegeben und die Reaktionslösung für 6 h bei 25 °C gerührt. Die Lösungsmittel wurden unter reduziertem Druck entfernt und der verbleibende Rückstand mittels HPLC chromatographisch aufgetrennt. So konnten 24 mg (99% Reinheit, 18% Ausbeute) des N-Ethyl-N-[2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin-5-yl]methansulfonamids erhalten werden.
1H-NMR(400MHz, CDCl3): δ = 9,29 (s, 1 H), 8,77 - 8.76 (m, 1 H), 8,39 - 8,32 (m, 2 H), 7,62 - 7,59 (m, 1 H), 7,50 - 7,47 (m, 1 H), 4,07 - 4,02 (m, 2 H), 3,09 (s, 3 H), 1,26 - 1,22 (m, 3 H).To a solution of N-ethyl-2- (pyridin-3-yl) [1,3] thiazolo [5,4-b] pyridine-5-amine (103 mg, 0.40 mmol) in THF (4 mL) Lithium hexamethyldisilazide (1.2 mL, 1.2 mmol, 1 M in THF) was added at -20 ° C and the reaction mixture was stirred for 10 min. Subsequently, methanesulfonyl chloride (0.14 g, 1.2 mmol) was added and the reaction solution was stirred for 6 h at 25 ° C. The solvents were removed under reduced pressure and the remaining residue was chromatographed by HPLC. Thus, 24 mg (99% purity, 18% yield) of the N- ethyl N - [2- (pyridin-3-yl) [1,3] thiazolo [5,4-b] pyridin-5-yl] methanesulfonamide to be obtained.
1 H-NMR (400MHz, CDCl 3): δ = 9.29 (s, 1 H), 8.77 - 8.76 (m, 1 H), 8.39 - 8.32 (m, 2 H), 7 , 62-7.59 (m, 1H), 7.50-7.47 (m, 1H), 4.07-4.02 (m, 2H), 3.09 (s, 3H) , 1.26-1.22 (m, 3H).

Beispiel 30: N-Methyl-3-(methylsulfonyl)-N-[2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin-5-yl]propanamid Example 30: N-Methyl-3- (methylsulfonyl) -N- [2- (pyridin-3-yl) [1,3] thiazolo [5,4-b] pyridin-5-yl] propanamide

Figure imgb0299
Figure imgb0299

Eine Lösung von 3-(Methylsulfanyl)-N-[2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin-5-yl]propanamid (1.0 Äq) und meta-Chlorperbenzoesäure (2.0 Äq) in CH2Cl2 (5 mL) wurde für 16 h bei 30 °C gerührt. Das Lösungsmittel wurde unter reduziertem Druck entfernt und der Rückstand mittels HPLC aufgereinigt (Laufmittel enthält Ameisensäure). So wurde 3-(Methylsulfonyl)-N-[2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin-5-yl]propanamid erhalten.A solution of 3- (methylsulfanyl) -N- [2- (pyridin-3-yl) [1,3] thiazolo [5,4-b] pyridin-5-yl] propanamide (1.0 eq) and meta- chloroperbenzoic acid ( 2.0 eq) in CH 2 Cl 2 (5 mL) was stirred for 16 h at 30 ° C. The solvent was removed under reduced pressure and the residue purified by HPLC (eluent containing formic acid). There was thus obtained 3- (methylsulfonyl) -N- [2- (pyridin-3-yl) [1,3] thiazolo [5,4-b] pyridin-5-yl] propanamide.

Zu einer Lösung des 3-(Methylsulfonyl)-N-[2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin-5-yl]propanamids (1.0 Äq.) in Dimethylformamid (4 mL) wurde Natriumhydrid (1,1 Äq.) gegeben und die Mischung für 30 min bei 0 °C gerührt. Anschließend wurde Methyliodid (1,0 Äq.) zugesetzt und die Mischung für weitere 30 min bei 0 °C gerührt. Die Reaktionsmischung wurde mit einer gesättigen wässrigen Lösung von Ammoniumchlorid (1 mL) versetzt und das Lösungsmittel unter reduziertem Druck entfernt. Zur Isolation des N-Methyl-3-(methylsulfonyl)-N-[2-(pyridin-3-yl)[1,3]thiazolo[5,4-b]pyridin-5-yl]propanamids wurde die Reaktionsmischung per HPLC aufgereinigt (Laufmittel enthält Ameisensäure).
1H-NMR(400,0 MHz, DMSO): δ= 9,299(2,1); 9,295(2,1); 8,802(1,5); 8,792(1,5); 8,595(3,3); 8,573(3,5); 8,499(1,1); 8,494(1,5); 8,489(1,1); 8,479(1,2); 8,474(1,6); 8,469(1,1); 7,819(3,2); 7,797(3,0); 7,669(1,3); 7,657(1,3); 7,649(1,3); 7,637(1,2); 3,902(3,7); 3,431(2,9); 3,423(14,8); 3,414(4,1); 3,394(2,7); 3,330(150,6); 3,176(0,7); 3,163(0,7); 2,991(16,0); 2,931(1,6); 2,912(2,3); 2,893(1,3); 2,676(0,6); 2,672(0,8); 2,667(0,6); 2,525(2,2); 2,511(46,0); 2,507(94,4); 2,502(130,3); 2,498(97,4); 2,494(47,0); 2,334(0,5); 2,329(0,7); 2,325(0,6); 0,000(2,9)To a solution of the 3- (methylsulfonyl) -N- [2- (pyridin-3-yl) [1,3] thiazolo [5,4-b] pyridin-5-yl] propanoamide (1.0 eq.) In dimethylformamide ( 4 mL) was added sodium hydride (1.1 eq.) And the mixture was stirred at 0 ° C for 30 min. Then, methyl iodide (1.0 eq.) Was added and the mixture was stirred at 0 ° C for a further 30 min. The reaction mixture was added with a saturated aqueous solution of ammonium chloride (1 mL), and the solvent was removed under reduced pressure. For isolation of the N-methyl-3- (methylsulfonyl) -N- [2- (pyridin-3-yl) [1,3] thiazolo [5,4-b] pyridin-5-yl] propanamide the reaction mixture was purified by HPLC (eluant contains formic acid).
1 H-NMR (400.0 MHz, DMSO): δ = 9.299 (2.1); 9,295 (2.1); 8,802 (1.5); 8,792 (1.5); 8,595 (3.3); 8.573 (3.5); 8,499 (1.1); 8,494 (1.5); 8,489 (1.1); 8.479 (1.2); 8.474 (1.6); 8.469 (1.1); 7,819 (3.2); 7,797 (3.0); 7.669 (1.3); 7,657 (1.3); 7.649 (1.3); 7,637 (1.2); 3,902 (3.7); 3,431 (2.9); 3,423 (14.8); 3,414 (4.1); 3,394 (2.7); 3.330 (150.6); 3,176 (0.7); 3,163 (0.7); 2,991 (16.0); 2,931 (1.6); 2,912 (2.3); 2,893 (1.3); 2,676 (0.6); 2,672 (0.8); 2,667 (0.6); 2,525 (2.2); 2,511 (46.0); 2,507 (94.4); 2.502 (130.3); 2,498 (97.4); 2,494 (47.0); 2,334 (0.5); 2,329 (0.7); 2,325 (0.6); 0.000 (2.9)

Verbindungen der Formel (I) und auch solche, die nicht unter die Formel (I) fallen, sind in der folgenden Tabelle aufgeführt. Auch die nicht unter die Formel (I) fallenden Verbindungen sind Gegenstand der Erfindung. Tabelle 1 Verbindungen der Formel

Figure imgb0300
Verbindungs-Nr. A R1 R2 1
Figure imgb0301
 H
Figure imgb0302
 2
Figure imgb0303
 H
Figure imgb0304
 3
Figure imgb0305
 H
Figure imgb0306
 4
Figure imgb0307
 H
Figure imgb0308
 6
Figure imgb0309
 H
Figure imgb0310
 7
Figure imgb0311
 H
Figure imgb0312
 8
Figure imgb0313
 H
Figure imgb0314
 9
Figure imgb0315
 H
Figure imgb0316
 10
Figure imgb0317
 H
Figure imgb0318
 11
Figure imgb0319
 H
Figure imgb0320
 12
Figure imgb0321
 H
Figure imgb0322
 13
Figure imgb0323
 H
Figure imgb0324
 14
Figure imgb0325
 H
Figure imgb0326
 15
Figure imgb0327
 H
Figure imgb0328
 16
Figure imgb0329
 H
Figure imgb0330
 17
Figure imgb0331
 H
Figure imgb0332
 18
Figure imgb0333
 H
Figure imgb0334
 19
Figure imgb0335
 H
Figure imgb0336
 20*
Figure imgb0337
 H
Figure imgb0338
 21*
Figure imgb0339
 H
Figure imgb0340
 22
Figure imgb0341
 H
Figure imgb0342
 23*
Figure imgb0343
 H
Figure imgb0344
 24*
Figure imgb0345
 H
Figure imgb0346
 25*
Figure imgb0347
 H
Figure imgb0348
 26*
Figure imgb0349
 H
Figure imgb0350
 27*
Figure imgb0351
 H
Figure imgb0352
 28*
Figure imgb0353
 H
Figure imgb0354
 29
Figure imgb0355
 H
Figure imgb0356
 30
Figure imgb0357
 H
Figure imgb0358
 31
Figure imgb0359
 H
Figure imgb0360
 32
Figure imgb0361
 H
Figure imgb0362
 33
Figure imgb0363
 H
Figure imgb0364
 34
Figure imgb0365
 H
Figure imgb0366
 35
Figure imgb0367
 H
Figure imgb0368
 36
Figure imgb0369
 H
Figure imgb0370
 37
Figure imgb0371
 H
Figure imgb0372
 38
Figure imgb0373
 H
Figure imgb0374
 39
Figure imgb0375
 H
Figure imgb0376
 40
Figure imgb0377
 H
Figure imgb0378
 42
Figure imgb0379
 H
Figure imgb0380
 Mit einem * markierte Verbindungen wurden als Salz der Ameisensäure isoliert und als solche charakterisiert sowie biologisch getestet. Compounds of the formula (I) and also those which do not fall under the formula (I) are listed in the following table. Also not falling under the formula (I) compounds are the subject of the invention. <b><u> Table 1 </ u></b> Compounds of the formula
Figure imgb0300
 Com. A R 1 R 2 1
Figure imgb0301
 H
Figure imgb0302
 2
Figure imgb0303
 H
Figure imgb0304
 3
Figure imgb0305
 H
Figure imgb0306
 4
Figure imgb0307
 H
Figure imgb0308
 6
Figure imgb0309
 H
Figure imgb0310
 7
Figure imgb0311
 H
Figure imgb0312
 8th
Figure imgb0313
 H
Figure imgb0314
 9
Figure imgb0315
 H
Figure imgb0316
 10
Figure imgb0317
 H
Figure imgb0318
 11
Figure imgb0319
 H
Figure imgb0320
 12
Figure imgb0321
 H
Figure imgb0322
 13
Figure imgb0323
 H
Figure imgb0324
 14
Figure imgb0325
 H
Figure imgb0326
 15
Figure imgb0327
 H
Figure imgb0328
 16
Figure imgb0329
 H
Figure imgb0330
 17
Figure imgb0331
 H
Figure imgb0332
 18
Figure imgb0333
 H
Figure imgb0334
 19
Figure imgb0335
 H
Figure imgb0336
 20 *
Figure imgb0337
 H
Figure imgb0338
 21 *
Figure imgb0339
 H
Figure imgb0340
 22
Figure imgb0341
 H
Figure imgb0342
 23 *
Figure imgb0343
 H
Figure imgb0344
 24 *
Figure imgb0345
 H
Figure imgb0346
 25 *
Figure imgb0347
 H
Figure imgb0348
 26 *
Figure imgb0349
 H
Figure imgb0350
 27 *
Figure imgb0351
 H
Figure imgb0352
 28 *
Figure imgb0353
 H
Figure imgb0354
 29
Figure imgb0355
 H
Figure imgb0356
 30
Figure imgb0357
 H
Figure imgb0358
 31
Figure imgb0359
 H
Figure imgb0360
 32
Figure imgb0361
 H
Figure imgb0362
 33
Figure imgb0363
 H
Figure imgb0364
 34
Figure imgb0365
 H
Figure imgb0366
 35
Figure imgb0367
 H
Figure imgb0368
 36
Figure imgb0369
 H
Figure imgb0370
 37
Figure imgb0371
 H
Figure imgb0372
 38
Figure imgb0373
 H
Figure imgb0374
 39
Figure imgb0375
 H
Figure imgb0376
 40
Figure imgb0377
 H
Figure imgb0378
 42
Figure imgb0379
 H
Figure imgb0380
 Compounds labeled with a * were isolated as a salt of formic acid and characterized as such and biologically tested.

Die Beispiele 1-4 fallen nicht unter den Schutzumfang und sind als Vergleichsbeispiele anzusehen. Tabelle 2 Analytische Daten zu den angegebenen Verbindungen. Bsp.-Nr. logP[ a] logP[b ] 1H-NMR [σ (ppm)] bzw. LC-MS [m/z] 1 4,81 4,75 1H-NMR(400,0 MHz, d6-DMSO): δ = 9,336(9,6); 9,331(9,4); 9,330(9,2); 8,819(7,7); 8,815(8,5); 8,807(8,3); 8,803(8,5); 8,615(14,3); 8,593(16,0); 8,536(4,4); 8,532(5,7); 8,530(5,6); 8,526(4,5); 8,516(4,8); 8,512(5,8); 8,510(6,2); 8,506(4,6); 8,318(0,8); 8,208(9,7); 8,188(9,7); 8,040(6,9); 8,036(7,9); 8,018(7,2); 8,014(6,9); 7,685(5,6); 7,683(5,7); 7,673(5,4); 7,671(5,5); 7,665(5,4); 7,663(5,4); 7,653(5,3); 7,651(5,4); 7,423(8,2); 7,411(0,5); 7,392(8,1); 4,008(4,2); 3,982(13,4); 3,956(14,0); 3,930(4,8); 3,330(261,5); 2,682(0,7); 2,677(1,5); 2,673(2,1); 2,668(1,6); 2,664(0,8); 2,656(0,3); 2,526(5,6); 2,521(8,5); 2,512(114,8); 2,508(235,5); 2,504(315,5); 2,499(263,2); 2,420(1,4); 2,368(0,5); 2,335(1,8); 2,330(2,1); 2,326(1,6); 2,321(0,9); 1,990(0,6); 1,398(4,1); 0,146(2,5); 0,029(0,4); 0,008(19,6); 0,000(555,1); -0,009(21,4); -0,033(0,4); -0,150(2,6). 2 4,67 4,64 1H-NMR(400,0 MHz, d6-DMSO): δ = 9,322(1,9); 8,808(1,4); 8,799(1,4); 8,591(4,3); 8,581(0,4); 8,569(5,1); 8,560(0,4); 8,516(1,3); 8,511(1,9); 8,507(1,4); 8,496(1,4); 8,491(2,0); 8,487(1,4); 8,317(0,5); 8,307(3,9); 8,301(7,3); 8,279(4,2); 8,070(2,2); 8,066(2,1); 8,050(2,2); 8,046(2,2); 7,677(1,7); 7,666(1,7); 7,658(1,6); 7,646(1,6); 7,456(3,0); 7,436(2,8); 4,156(1,3); 4,130(4,2); 4,104(4,4); 4,078(1,5); 3,331(95,2); 2,677(0,4); 2,673(0,6); 2,668(0,5); 2,526(1,4); 2,512(35,3); 2,508(70,8); 2,504(93,0); 2,499(68,9); 2,495(34,7); 2,455(16,0); 2,391(0,8); 2,340(0,4); 2,335(0,5); 2,330(0,7); 2,326(0,5); 1,397(3,2); 0,008(0,4); 0,000(11,3); -0,008(0,5). 3 3,02 3,09 1H-NMR(400,0 MHz, d6-DMSO): δ = 9,341(3,3); 9,336(3,3); 8,823(2,3); 8,820(2,6); 8,811(2,5); 8,808(2,6); 8,654(3,6); 8,633(4,0); 8,593(0,4); 8,581(3,0); 8,562(3,0); 8,535(2,0); 8,530(1,5); 8,519(1,5); 8,514(2,0); 8,510(1,5); 8,317(0,4); 8,126(2,1); 8,122(2,4); 8,104(2,1); 8,101(2,1); 7,687(1,8); 7,675(1,9); 7,667(1,8); 7,655(1,7); 7,526(2,5); 7,496(2,5); 5,757(2,9); 4,261(0,4); 4,251(0,6); 4,232(1,0); 4,224(1,7); 4,205(1,9); 4,197(1,9); 4,178(1,7); 4,169(1,0); 4,150(0,6); 4,141(0,4); 3,329(81,5); 2,672(1,0); 2,668(0,8); 2,507(113,6); 2,503(144,6); 2,499(114,9); 2,468(16,0); 2,429(0,4); 2,330(1,0); 0,000(17,6). 4 2,99 2,98 1H-NMR(400,0 MHz, d6-DMSO): δ = 9,325(3,3); 9,320(3,3); 8,813(2,4); 8,810(2,6); 8,802(2,5); 8,798(2,6); 8,717(4,0); 8,713(4,2); 8,629(3,7); 8,607(4,3); 8,522(1,4); 8,517(2,0); 8,512(1,5); 8,502(1,5); 8,497(2,1); 8,492(1,4); 8,338(2,3); 8,331(5,1); 8,318(2,6); 8,310(4,1); 7,680(1,8); 7,668(1,8); 7,660(1,8); 7,648(1,7); 7,552(2,9); 7,532(2,8); 5,758(0,9); 4,235(0,7); 4,226(0,7); 4,208(2,0); 4,199(1,9); 4,181(2,0); 4,172(2,0); 4,154(0,7); 4,145(0,7); 4,136(0,3); 3,366(0,3); 3,331(76,2); 2,672(0,7); 2,507(78,8); 2,503(100,7); 2,499(78,2); 2,460(16,0); 2,330(0,7); 0,000(2,6). 6 2,53 2,97 1H-NMR(400,0 MHz, d6-DMSO): δ = 9,151(5,5); 9,147(5,6); 8,683(3,9); 8,679(4,2); 8,671(4,1); 8,667(4,1); 8,335(0,5); 8,327(2,5); 8,323(3,4); 8,318(2,6); 8,314(1,6); 8,307(2,7); 8,302(3,5); 8,298(2,5); 8,140(8,2); 8,118(8,6); 7,580(3,1); 7,569(3,1); 7,561(3,1); 7,549(2,9); 7,521(0,4); 6,731(7,9); 6,708(7,7); 5,754(1,8); 3,510(5,5); 3,494(14,2); 3,477(5,8); 3,316(134,8); 3,141(0,9); 2,675(1,7); 2,671(2,3); 2,666(1,7); 2,632(1,8); 2,571(0,4); 2,567(0,4); 2,562(0,4); 2,524(7,4); 2,510(135,4); 2,506(268,7); 2,502(352,7); 2,497(264,6); 2,493(136,1); 2,333(1,6); 2,328(2,2); 2,324(1,7); 2,018(0,7); 2,003(6,0); 1,993(7,0); 1,986(16,0); 1,980(7,3); 1,970(5,9); 1,335(0,8); 1,259(0,7); 1,250(0,6); 1,233(2,1); 0,854(0,4); 0,146(2,1); 0,031(0,4); 0,022(0,8); 0,008(17,8); 0,000(454,2); -0,008(23,0); -0,028(0,7); -0,150(2,2). 7 1,43 1,50 1H-NMR(400,0 MHz, d6-DMSO): δ = 9,357(3,1); 9,352(3,1); 9,049(8,9); 9,037(9,0); 8,829(2,3); 8,825(2,5); 8,817(2,4); 8,813(2,4); 8,667(16,0); 8,564(1,3); 8,560(1,9); 8,555(1,4); 8,544(1,4); 8,539(1,9); 8,535(1,3); 8,319(0,7); 7,690(1,7); 7,678(1,7); 7,671(1,7); 7,659(1,6); 7,634(2,5); 7,622(4,7); 7,610(2,4); 5,759(1,0); 3,330(115,0); 2,676(1,3); 2,672(1,7); 2,667(1,3); 2,525(4,6); 2,507(204,2); 2,503(264,8); 2,498(196,5); 2,334(1,3); 2,329(1,7); 2,325(1,3); 1,258(0,5); 1,233(1,9); 0,852(0,6); 0,833(0,3); 0,146(0,6); 0,008(4,5); 0,000(124,1); -0,150(0,6). 8 2,12 2,68 1H-NMR(601,6 MHz, CDCl3): δ = 9,345(6,9); 9,344(7,1); 9,342(7,2); 9,341(6,4); 8,772(5,8); 8,769(5,9); 8,764(6,0); 8,762(5,7); 8,737(3,9); 8,736(4,6); 8,734(4,6); 8,733(4,0); 8,729(4,2); 8,728(4,6); 8,727(4,4); 8,725(3,6); 8,648(12,4); 8,634(14,1); 8,511(4,7); 8,510(6,8); 8,508(4,3); 8,498(4,9); 8,497(7,1); 8,495(4,3); 8,426(15,6); 8,422(5,2); 8,421(4,8); 8,418(3,8); 8,412(16,0); 8,409(5,6); 8,408(5,0); 8,405(3,7); 7,883(3,5); 7,880(3,4); 7,870(5,6); 7,868(5,5); 7,857(3,6); 7,854(3,4); 7,498(4,4); 7,496(4,2); 7,490(4,5); 7,488(4,3); 7,484(4,4); 7,483(4,1); 7,477(4,3); 7,475(4,0); 7,434(0,3); 7,369(3,9); 7,368(3,8); 7,362(3,9); 7,360(4,1); 7,357(4,1); 7,355(3,7); 7,349(3,7); 7,347(3,4); 7,262(58,9); 7,086(0,3); 1,594(59,7); 1,333(0,7); 1,284(1,0); 1,254(1,5); 0,880(0,3); 0,844(0,4); 0,839(0,4); 0,005(1,5); 0,000(45,7); -0,006(1,7). 9 3,99 4,06 1H-NMR(400,0 MHz, d6-DMSO): δ = 9,638(3,9); 9,195(2,9); 9,191(3,0); 8,717(2,3); 8,713(2,4); 8,705(2,4); 8,701(2,4); 8,378(1,2); 8,374(1,7); 8,368(1,3); 8,358(1,4); 8,353(1,8); 8,348(1,4); 8,318(0,4); 8,236(4,2); 8,214(4,5); 8,007(3,2); 8,002(3,3); 7,607(1,7); 7,595(1,6); 7,587(1,6); 7,573(2,1); 7,571(2,0); 7,565(1,7); 7,550(2,0); 7,545(2,0); 7,236(2,9); 7,215(2,5); 7,038(4,0); 7,015(4,0); 4,056(0,4); 4,038(1,1); 4,020(1,1); 4,002(0,4); 3,954(1,2); 3,928(3,7); 3,902(3,9); 3,876(1,3); 3,330(134,6); 2,676(0,8); 2,672(1,1); 2,667(0,8); 2,525(3,4); 2,511(66,4); 2,507(131,9); 2,503(172,2); 2,498(126,1); 2,494(63,2); 2,338(16,0); 2,266(0,5); 1,989(4,8); 1,397(0,4); 1,193(1,3); 1,175(2,5); 1,157(1,3); 0,146(0,9); 0,008(7,6); 0,000(197,5); -0,008(8,7); -0,150(0,9). 10 2,65 2,69 1H-NMR(400,0 MHz, d6-DMSO): δ = 9,354(8,2); 9,352(8,9); 9,348(8,9); 9,346(8,5); 8,849(7,2); 8,845(7,8); 8,837(7,7); 8,833(7,7); 8,781(8,4); 8,780(8,4); 8,760(9,1); 8,759(9,0); 8,561(4,4); 8,557(5,5); 8,556(5,3); 8,551(4,4); 8,541(4,8); 8,537(5,5); 8,535(5,8); 8,531(4,5); 8,151(16,0); 8,130(15,0); 7,700(5,4); 7,698(5,5); 7,688(5,2); 7,686(5,3); 7,680(5,2); 7,678(5,2); 7,668(5,1); 7,666(5,1); 3,338(38,7); 2,681(0,3); 2,677(0,5); 2,672(0,3); 2,530(1,2); 2,525(1,7); 2,517(26,2); 2,512(54,4); 2,508(72,0); 2,503(51,8); 2,499(24,7); 2,339(0,3); 2,334(0,5); 2,330(0,3); 1,993(0,4); 1,225(1,4); 0,008(0,9); 0,000(30,6); -0,009(1,0). 11 2,10 1,95 1H-NMR(400,0 MHz, d6-DMSO): δ = 9,179(5,8); 9,174(5,8); 8,709(4,1); 8,706(4,4); 8,697(4,3); 8,694(4,2); 8,356(3,6); 8,336(3,7); 8,317(0,4); 8,222(6,4); 8,199(6,7); 7,598(3,3); 7,586(3,4); 7,578(3,3); 7,566(3,0); 7,138(6,3); 7,115(6,1); 3,745(9,6); 3,733(16,0); 3,721(13,6); 3,609(13,4); 3,596(15,7); 3,585(9,5); 3,332(188,8); 2,672(1,2); 2,503(168,0); 2,330(1,1); 1,990(0,5); 0,000(15,6). 12 4,81 4,78 1H-NMR(601,6 MHz, CDCl3): δ = 9,227(1,6); 9,224(1,6); 8,677(1,1); 8,674(1,2); 8,669(1,2); 8,666(1,1); 8,297(0,8); 8,293(1,1); 8,290(0,8); 8,283(0,8); 8,280(1,1); 8,277(0,8); 7,901(2,9); 7,885(2,9); 7,424(1,0); 7,423(1,0); 7,413(2,4); 7,410(2,9); 7,403(1,0); 7,402(0,9); 7,310(1,5); 7,296(1,8); 7,264(3,3); 7,164(1,4); 7,160(1,3); 7,151(1,1); 7,147(1,1); 6,627(2,9); 6,611(2,9); 5,299(2,2); 3,545(1,4); 3,538(16,0); 3,438(1,1); 3,422(3,4); 3,406(3,5); 3,391(1,2); 2,491(10,7); 2,442(1,0); 2,359(0,7); 1,688(1,5); 1,254(1,6); 0,000(0,9). 13 3,82 3,72 1H-NMR(400,0 MHz, d6-DMSO): δ = 9,397(12,4); 9,334(8,8); 9,330(8,9); 8,819(6,7); 8,816(7,5); 8,807(7,2); 8,804(7,4); 8,747(14,6); 8,725(16,0); 8,538(3,9); 8,533(5,4); 8,528(4,1); 8,518(4,3); 8,512(5,7); 8,508(4,3); 8,382(15,9); 8,317(2,8); 8,235(15,5); 8,213(14,5); 7,992(0,5); 7,684(5,1); 7,682(5,3); 7,672(4,9); 7,670(5,1); 7,664(4,9); 7,662(5,0); 7,652(4,7); 7,650(4,8); 3,329(899,6); 2,676(4,4); 2,672(6,1); 2,667(4,6); 2,542(2,4); 2,525(16,4); 2,520(24,9); 2,511(334,7); 2,507(693,8); 2,503(925,4); 2,498(682,8); 2,494(341,5); 2,334(4,3); 2,329(6,0); 2,325(4,5); 2,075(0,3); 1,148(0,6); 0,146(7,1); 0,032(1,0); 0,025(2,1); 0,008(54,7); 0,000(1562,0); -0,009(65,0); -0,029(1,5); -0,038(0,8); -0,042(0,6); -0,050(0,5);-0,065(0,4); -0,150(7,1). 14 1H-NMR(400MHz, CDCl3): δ = 9,23 (s, 1 H), 8,68 - 8,67 (m, 1 H), 8,29 - 8,26 (m, 1 H), 8,12 - 8,09 (m, 1 H), 7,43 - 7,40 (m, 1 H), 6,96 - 6,94 (m, 1 H), 5,25 (s, 1 H), 2,66 - 2,62 (m, 1 H), 0,89 - 0,86 (m, 2 H), 0,65 - 0,63 (m, 2 H). 15 1,34 16 1H-NMR(400MHz, CDCl3): δ = 9,13 (s, 1 H), 8,77 - 8,76 (m, 1 H), 8,38 - 8,31 (m, 2 H), 7,59 - 7,57 (m, 1 H), 7,50 - 7,47 (m, 1 H), 3,54 (s, 3 H), 1,73 - 1,70 (m, 1 H), 1,18 - 1,14 (m, 2 H), 0,84 - 0,80 (m, 2 H). 17 1H-NMR(400MHz, CDCl3): δ = 9,29 (s, 1 H), 8,77 - 8.76 (m, 1 H), 8,39 - 8,32 (m, 2 H), 7,62 - 7,59 (m, 1 H), 7,50 - 7,47 (m, 1 H), 4,07 - 4,02 (m, 2 H), 3,09 (s, 3 H), 1,26 - 1,22 (m, 3 H). 18 1H-NMR(400MHz, CDCl3): δ = 9,14 (s, 1 H), 8,60 - 8,58 (m, 1 H), 8,21 - 8,18 (m, 1 H), 7,94 - 7,92 (m, 1 H), 7,38 - 7,32 (m, 1 H), 6,48 - 6,46 (m, 1 H), 4,64 (s, 1 H), 3,40 - 3,37 (m, 2 H), 1,25 - 1,22 (m, 3 H). 19 1H-NMR(400MHz, CDCl3): δ = 9,24 (s, 1 H), 8,70 - 8,69 (m, 1 H), 8,32 - 8,25 (m, 2 H), 7,46 - 7,39 (m, 2 H), 4,03 - 3,98 (m, 2 H), 1,50 - 1,48 (m, 1 H), 1,18 - 1,15 (m, 3 H), 1,09 - 1,07 (m, 2 H), 0,71 - 0,70 (m, 2 H). 20 1,37 1H-NMR(400,0 MHz, d6-DMSO): δ = 9,314(2,4); 8,816(1,7); 8,807(1,8); 8,628(5,0); 8,606(5,4); 8,510(1,6); 8,505(2,4); 8,501(1,8); 8,491(1,9); 8,485(2,6); 8,481(1,9); 8,310(0,4); 7,779(5,8); 7,758(5,6); 7,678(1,8); 7,666(1,9); 7,658(1,9); 7,646(1,8); 3,902(16,0); 3,585(1,0); 3,565(0,9); 3,508(0,5); 3,392(22,5); 3,352(536,8); 3,291(2,1); 3,278(2,7); 3,257(2,4); 3,240(1,3); 3,225(3,3); 3,208(2,3); 3,202(2,9); 3,191(2,2); 3,176(1,8); 3,169(1,5); 3,058(0,9); 3,034(1,2); 3,025(0,9); 3,014(1,1); 3,001(1,0); 2,982(0,7); 2,872(0,5); 2,860(0,5); 2,678(1,0); 2,673(1,3); 2,669(1,0); 2,527(3,5); 2,513(74,3); 2,509(156,7); 2,504(219,6); 2,500(164,1); 2,495(78,1); 2,336(1,0); 2,331(1,4); 2,326(1,1); 2,309(0,5); 2,293(0,9); 2,277(1,1); 2,264(0,9); 2,246(1,2); 2,222(1,5); 2,213(0,5); 2,203(1,4); 2,189(0,8); 2,179(0,7); 2,170(0,7); 2,143(0,9); 0,000(3,0) 21 3,39 1H-NMR(400,0 MHz, d6-DMSO): δ = 9,239(2,3); 8,766(1,5); 8,755(1,6); 8,477(2,7); 8,435(12,4); 8,420(1,8); 8,413(1,9); 8,410(2,2); 7,881(1,3); 7,861(1,5); 7,675(1,5); 7,655(3,0); 7,636(1,9); 7,620(1,2); 4,172(16,0); 3,901(7,5); 3,550(0,8); 3,508(0,7); 3,363(521,7); 3,355(877,8); 3,177(0,8); 3,164(0,8); 2,673(1,5); 2,509(170,4); 2,504(235,5); 2,500(187,4); 2,331(1,3); 0,000(2,2) 22 1,98 1H-NMR(400,0 MHz, d6-DMSO): δ = 9,301(1,3); 8,807(0,9); 8,797(0,9); 8,574(2,8); 8,552(3,0); 8,496(0,9); 8,491(1,5); 8,487(0,9); 8,476(0,9); 8,470(1,4); 7,789(2,5); 7,767(2,4); 7,670(0,9); 7,658(1,0); 7,650(1,0); 7,638(0,9); 3,902(2,8); 3,417(0,4); 3,392(13,0); 3,336(158,8); 3,329(84,5); 2,767(1,4); 2,714(10,8); 2,677(0,5); 2,672(0,6); 2,668(0,4); 2,512(34,0); 2,508(69,0); 2,503(95,5); 2,499(72,2); 2,494(35,4); 2,334(0,4); 2,330(0,5); 2,326(0,4); 2,102(2,6); 2,000(16,0); 0,000(1,7) 23 1,71 1H-NMR(400,0 MHz, d6-DMSO): δ = 9,295(2,6); 8,804(1,8); 8,795(1,8); 8,548(6,3); 8,526(6,8); 8,491(1,7); 8,486(2,5); 8,481(1,8); 8,471(1,8); 8,466(2,6); 8,461(1,7); 7,794(5,6); 7,772(5,4); 7,669(1,9); 7,656(1,9); 7,649(1,9); 7,637(1,8); 3,902(4,8); 3,509(0,4); 3,381(33,0); 3,344(337,1); 2,677(0,7); 2,673(1,0); 2,669(0,7); 2,526(2,7); 2,512(56,7); 2,508(118,3); 2,504(166,3); 2,499(127,2); 2,495(63,3); 2,459(2,0); 2,441(6,0); 2,422(6,1); 2,404(2,0); 2,335(0,7); 2,331(0,9); 2,326(0,7); 1,042(7,8); 1,024(16,0); 1,005(7,4); 0,000(1,1) 24 1,22 1H-NMR(400,0 MHz, d6-DMSO): δ = 9,332(1,3); 8,827(0,9); 8,817(0,9); 8,612(3,9); 8,591(4,1); 8,537(0,9); 8,532(1,1); 8,527(0,9); 8,517(0,9); 8,512(1,2); 8,507(0,8); 7,801(4,0); 7,780(3,8); 7,690(0,9); 7,678(0,9); 7,670(0,9); 7,658(0,8); 3,902(2,5); 3,359(205,8); 3,170(0,6); 3,063(14,1); 3,001(16,0); 2,868(1,7); 2,678(0,3); 2,673(0,5); 2,669(0,4); 2,527(1,3); 2,513(28,2); 2,509(59,8); 2,504(84,0); 2,500(62,4); 2,495(29,6); 2,335(0,3); 2,331(0,5); 2,326(0,4); 1,275(0,6); 1,260(1,1); 1,245(0,9); 0,000(1,3) 25 4,33 1H-NMR(400,0 MHz, d6-DMSO): δ = 11,171(13,2); 9,386(7,1); 8,851(4,9); 8,840(5,0); 8,732(13,9); 8,711(16,0); 8,587(3,8); 8,582(5,8); 8,577(4,4); 8,567(4,2); 8,562(6,0); 8,558(4,4); 8,459(11,7); 8,395(15,4); 8,374(14,2); 8,312(0,5); 8,186(5,6); 8,166(6,1); 7,708(4,6); 7,696(4,7); 7,688(4,7); 7,676(4,2); 7,586(5,2); 7,566(11,4); 7,546(7,8); 7,496(8,3); 7,477(5,1); 4,100(0,3); 3,902(14,2); 3,762(0,3); 3,722(0,4); 3,711(0,4); 3,698(0,4); 3,688(0,4); 3,657(0,5); 3,638(0,5); 3,600(0,6); 3,569(0,7); 3,508(1,4); 3,344(1201,2); 3,216(0,3); 3,176(1,0); 3,164(0,9); 2,678(2,3); 2,673(3,3); 2,669(2,5); 2,623(0,4); 2,612(0,5); 2,509(393,5); 2,504(550,6); 2,500(436,2); 2,335(2,1); 2,331(3,0); 2,326(2,3); 1,249(0,4); 1,232(0,8); 0,000(8,0) 26 2,09 1H-NMR(400,0 MHz, d6-DMSO): δ = 9,358(4,8); 9,308(1,8); 9,292(3,6); 9,276(1,8); 8,840(3,2); 8,829(3,3); 8,677(7,2); 8,655(8,0); 8,558(3,4); 8,537(3,6); 8,293(7,7); 8,271(7,1); 7,696(2,8); 7,684(2,9); 7,676(2,9); 7,665(2,6); 3,902(6,4); 3,835(2,2); 3,818(2,3); 3,800(4,5); 3,784(4,5); 3,765(2,4); 3,749(2,3); 3,608(0,4); 3,540(0,5); 3,508(0,7); 3,347(684,3); 3,171(0,7); 2,674(1,5); 2,580(0,3); 2,509(182,9); 2,504(257,9); 2,500(208,8); 2,335(1,0); 2,331(1,4); 2,327(1,2); 2,282(0,6); 1,700(7,4); 1,653(16,0); 1,605(8,0); 1,208(0,6); 1,191(0,7); 0,000(3,0) 27 1,39 1H-NMR(400,0 MHz, d6-DMSO): δ = 9,334(4,4); 8,830(3,1); 8,820(3,2); 8,621(9,5); 8,600(10,3); 8,536(2,5); 8,531(4,1); 8,527(3,1); 8,516(2,9); 8,511(4,4); 8,507(3,2); 8,259(0,4); 7,856(2,8); 7,835(2,7); 7,688(3,1); 7,676(3,3); 7,668(3,4); 7,656(3,2); 4,563(0,5); 3,902(6,2); 3,705(16,0); 3,510(0,5); 3,343(495,0); 3,170(2,0); 2,991(0,4); 2,869(0,8); 2,857(0,8); 2,678(1,2); 2,673(1,5); 2,669(1,2); 2,526(4,1); 2,513(87,0); 2,508(182,5); 2,504(257,3); 2,499(197,4); 2,335(1,0); 2,331(1,4); 2,326(1,1); 0,000(2,0) 28 2,17 1H-NMR(400,0 MHz, d6-DMSO): δ = 9,640(2,6); 9,624(5,1); 9,607(2,5); 9,363(6,8); 8,843(4,7); 8,833(4,8); 8,689(9,4); 8,668(10,5); 8,563(4,8); 8,543(5,0); 8,303(10,4); 8,282(9,5); 7,698(3,8); 7,686(4,0); 7,679(4,0); 7,666(3,6); 4,167(1,6); 4,144(5,0); 4,127(5,3); 4,120(5,6); 4,103(5,0); 4,079(1,7); 3,902(16,0); 3,511(0,5); 3,337(468,1); 3,332(548,5); 3,170(0,9); 2,672(2,1); 2,503(356,0); 2,330(2,0); 1,234(0,4); 0,000(5,0) 29 2,23 1H-NMR(400,0 MHz, d6-DMSO): δ = 8,801(2,9); 8,436(2,8); 8,413(3,8); 8,392(1,7); 7,965(1,6); 7,945(1,8); 7,902(0,5); 7,889(0,3); 7,711(1,7); 7,692(2,0); 7,634(1,8); 7,623(1,7); 7,614(2,6); 7,588(1,1); 7,560(3,3); 7,527(3,1); 7,518(2,0); 7,505(3,1); 7,499(3,0); 7,480(1,2); 3,902(5,4); 3,550(16,0); 3,330(260,8); 3,269(0,4); 3,176(0,5); 3,163(0,5); 2,672(0,9); 2,503(158,8); 2,330(0,9); 0,000(1,6) 30 1,25 1H-NMR(400,0 MHz, d6-DMSO): δ = 9,299(2,1); 9,295(2,1); 8,802(1,5); 8,792(1,5); 8,595(3,3); 8,573(3,5); 8,499(1,1); 8,494(1,5); 8,489(1,1); 8,479(1,2); 8,474(1,6); 8,469(1,1); 7,819(3,2); 7,797(3,0); 7,669(1,3); 7,657(1,3); 7,649(1,3); 7,637(1,2); 3,902(3,7); 3,431(2,9); 3,423(14,8); 3,414(4,1); 3,394(2,7); 3,330(150,6); 3,176(0,7); 3,163(0,7); 2,991(16,0); 2,931(1,6); 2,912(2,3); 2,893(1,3); 2,676(0,6); 2,672(0,8); 2,667(0,6); 2,525(2,2); 2,511(46,0); 2,507(94,4); 2,502(130,3); 2,498(97,4); 2,494(47,0); 2,334(0,5); 2,329(0,7); 2,325(0,6); 0,000(2,9) 31 1,54 1H-NMR(400,0 MHz, d6-DMSO): δ = 8,800(2,2); 8,444(2,7); 8,422(2,9); 8,406(1,3); 8,391(1,3); 7,965(1,2); 7,945(1,3); 7,864(1,2); 7,844(1,5); 7,778(1,3); 7,759(1,9); 7,722(2,5); 7,687(1,7); 7,667(2,4); 7,648(1,0); 7,624(1,1); 7,607(1,4); 7,588(1,0); 7,550(2,8); 7,528(2,8); 4,110(0,5); 4,098(0,4); 3,902(6,4); 3,565(16,0); 3,348(372,1); 3,268(0,7); 3,176(3,3); 3,164(3,3); 2,673(0,9); 2,669(0,7); 2,512(54,0); 2,508(110,0); 2,504(151,7); 2,499(117,6); 2,495(60,1); 2,335(0,6); 2,331(0,8); 2,326(0,6); 0,000(1,0) 32 1,35 1H-NMR(400,0 MHz, d6-DMSO): δ = 9,353(3,1); 9,023(2,0); 9,011(2,0); 8,837(2,2); 8,829(2,3); 8,647(6,7); 8,625(7,6); 8,547(2,9); 8,527(3,1); 8,258(7,0); 8,236(6,4); 7,691(2,1); 7,680(2,4); 7,672(2,4); 7,660(2,2); 3,903(4,9); 3,339(296,0); 3,171(1,3); 2,992(0,6); 2,869(16,0); 2,857(16,0); 2,673(1,1); 2,543(1,0); 2,508(130,2); 2,504(180,0); 2,500(141,4); 2,331(1,0); 1,232(0,4); 1,214(0,4); 0,000(2,8) 33 1,53 1H-NMR(400,0 MHz, d6-DMSO): δ = 9,332(2,7); 8,829(1,9); 8,820(2,0); 8,608(4,4); 8,588(4,6); 8,586(4,6); 8,529(1,8); 8,524(2,7); 8,520(1,9); 8,509(1,9); 8,504(2,7); 8,500(1,9); 7,792(2,8); 7,782(3,6); 7,771(2,7); 7,761(3,4); 7,685(2,0); 7,673(2,1); 7,666(2,0); 7,654(1,8); 3,902(4,0); 3,558(1,0); 3,540(2,8); 3,522(2,9); 3,504(1,1); 3,340(362,1); 3,310(5,2); 3,292(3,8); 3,274(1,4); 3,029(16,0); 2,970(13,5); 2,869(0,3); 2,857(0,3); 2,678(0,7); 2,673(1,0); 2,669(0,7); 2,508(116,8); 2,504(164,6); 2,499(128,9); 2,335(0,6); 2,331(0,9); 2,326(0,7); 1,202(3,0); 1,184(6,4); 1,167(3,1); 1,154(3,6); 1,137(7,6); 1,119(3,3); 0,000(2,6) 34 2,10 1H-NMR(400,0 MHz, d6-DMSO): δ = 11,355(11,6); 9,384(0,4); 8,957(10,8); 8,936(0,4); 8,848(0,4); 8,768(8,5); 8,746(9,7); 8,719(0,5); 8,644(11,3); 8,564(0,3); 8,473(6,3); 8,457(6,5); 8,419(9,9); 8,397(9,1); 8,312(0,7); 8,293(5,6); 8,272(6,0); 8,111(5,9); 8,091(6,4); 7,900(1,4); 7,755(4,0); 7,735(8,8); 7,715(6,0); 7,689(4,9); 7,671(6,6); 7,650(10,0); 7,629(5,4); 7,567(0,6); 7,546(0,9); 7,527(0,4); 4,105(0,8); 4,095(0,9); 3,902(16,0); 3,716(0,4); 3,704(0,4); 3,676(0,4); 3,662(0,4); 3,623(0,4); 3,554(0,6); 3,542(0,7); 3,509(1,3); 3,340(958,2); 3,213(0,5); 3,177(4,7); 3,163(4,6); 2,673(3,4); 2,633(0,3); 2,503(584,4); 2,331(3,2); 1,233(1,2); 0,852(0,4); 0,831(0,4); 0,000(6,9) 35 2,03 1H-NMR(400,0 MHz, d6-DMSO): δ = 9,352(1,1); 9,166(0,4); 9,152(0,9); 9,137(0,4); 8,837(0,8); 8,827(0,8); 8,659(2,4); 8,638(2,7); 8,555(0,6); 8,550(0,9); 8,545(0,7); 8,535(0,7); 8,530(1,0); 8,525(0,6); 8,272(2,6); 8,251(2,4); 7,693(0,7); 7,681(0,8); 7,673(0,7); 7,661(0,7); 3,902(1,7); 3,565(0,8); 3,549(1,6); 3,530(1,6); 3,514(0,8); 3,346(153,5); 2,724(1,6); 2,705(2,3); 2,688(1,5); 2,678(0,4); 2,673(0,5); 2,669(0,3); 2,543(0,3); 2,526(1,2); 2,513(25,2); 2,508(52,8); 2,504(74,2); 2,499(56,0); 2,495(27,1); 2,331(0,4); 2,116(16,0); 0,000(1,2) 36 3,09 1H-NMR(400,0 MHz, d6-DMSO): δ = 11,332(8,4); 11,193(0,3); 9,382(5,3); 8,849(3,7); 8,839(3,7); 8,760(0,4); 8,739(8,4); 8,718(9,3); 8,646(7,3); 8,583(3,7); 8,563(3,9); 8,454(0,5); 8,404(9,3); 8,382(8,5); 8,310(0,5); 8,293(3,7); 8,272(3,9); 7,757(3,3); 7,737(7,3); 7,717(4,7); 7,708(3,2); 7,696(3,2); 7,688(3,3); 7,676(3,1); 7,649(5,1); 7,630(3,4); 3,902(16,0); 3,706(0,4); 3,509(1,6); 3,357(1127,4); 3,177(1,2); 3,164(1,1); 2,678(1,6); 2,674(2,2); 2,509(269,0); 2,505(368,5); 2,501(284,8); 2,336(1,5); 2,332(2,0); 1,233(1,1); 0,000(3,9) 37 2,61 1H-NMR(601,6 MHz, d6-DMSO): δ = 11,548(2,0); 8,828(6,7); 8,826(10,9); 8,824(6,7); 8,585(8,5); 8,570(11,0); 8,467(13,4); 8,452(11,2); 8,409(6,0); 8,408(6,0); 8,407(5,6); 8,400(16,0); 8,397(12,7); 8,291(5,9); 8,280(4,9); 8,278(6,0); 8,275(4,5); 7,996(5,9); 7,982(8,6); 7,981(9,0); 7,966(5,5); 7,735(5,8); 7,722(10,7); 7,709(5,1); 7,632(5,5); 7,621(6,3); 7,619(6,2); 7,608(5,1); 3,321(548,2); 2,617(2,2); 2,614(2,9); 2,611(2,1); 2,523(5,5); 2,520(6,8); 2,517(6,9); 2,508(164,2); 2,505(336,0); 2,502(450,5); 2,499(336,3); 2,496(163,1); 2,389(2,1); 2,386(2,8); 2,383(2,1); 1,233(0,4); 0,000(5,1) 38 1,18 1H-NMR(601,6 MHz, d6-DMSO): δ = 11,109(2,1); 9,259(2,2); 9,258(2,3); 9,255(2,3); 9,254(2,2); 8,771(1,9); 8,768(2,0); 8,763(2,0); 8,760(2,0); 8,502(3,5); 8,487(4,3); 8,457(1,1); 8,454(1,4); 8,453(1,3); 8,450(1,1); 8,444(1,2); 8,441(1,4); 8,440(1,5); 8,437(1,1); 8,339(1,1); 8,325(0,9); 7,638(1,3); 7,637(1,3); 7,630(1,3); 7,629(1,3); 7,625(1,4); 7,624(1,3); 7,617(1,3); 7,616(1,3); 3,481(1,8); 3,468(3,6); 3,456(2,1); 3,323(117,5); 3,040(16,0); 2,967(1,8); 2,954(3,0); 2,942(1,7); 2,617(0,4); 2,614(0,5); 2,611(0,4); 2,584(0,6); 2,542(0,9); 2,523(0,9); 2,520(1,1); 2,517(1,1); 2,508(28,3); 2,505(59,2); 2,502(80,0); 2,499(58,9); 2,496(27,9); 2,389(0,4); 2,386(0,5); 2,383(0,4); 0,000(1,1) 39 3,79 3,83 1H-NMR(601,6 MHz, CDCl3): δ = 9,317(0,8); 9,314(0,8); 8,782(0,6); 8,779(0,6); 8,774(0,6); 8,771(0,6); 8,695(0,7); 8,692(0,8); 8,460(1,3); 8,445(1,5); 8,404(0,4); 8,401(0,5); 8,398(0,4); 8,391(0,4); 8,388(0,5); 8,385(0,4); 8,273(1,5); 8,258(1,3); 7,506(0,5); 7,499(0,5); 7,498(0,5); 7,4934(0,5); 7,4925(0,5); 7,4854(0,4); 7,4845(0,4); 7,262(15,5); 6,776(1,0); 6,772(1,0); 5,301(0,5); 1,574(20,4); 1,423(0,5); 1,336(0,5); 1,333(0,5); 1,285(1,2); 1,254(16,0); 1,173(0,4); 1,160(0,3); 1,155(0,3); 1,106(0,5); 0,900(0,4); 0,892(1,1); 0,880(1,6); 0,868(1,0); 0,856(0,6); 0,840(1,1); 0,829(0,9); 0,714(0,4); 0,000(3,6) 40 2,26 2,33 1H-NMR(400,0 MHz, d6-DMSO): δ = 9,302(6,3); 9,300(7,0); 9,296(6,9); 9,294(6,7); 8,814(6,0); 8,810(6,6); 8,802(6,4); 8,798(6,5); 8,579(15,0); 8,558(15,8); 8,506(3,9); 8,502(4,6); 8,500(4,6); 8,496(3,9); 8,486(4,1); 8,482(4,6); 8,480(5,0); 8,476(3,9); 8,318(0,5); 7,761(16,0); 7,740(15,1); 7,672(4,6); 7,670(4,9); 7,660(4,5); 7,658(4,7); 7,652(4,4); 7,650(4,6); 7,640(4,3); 7,638(4,5); 3,330(93,2); 2,682(0,4); 2,677(0,8); 2,673(1,1); 2,668(0,8); 2,664(0,4); 2,526(2,7); 2,521(4,0); 2,513(58,2); 2,508(121,6); 2,503(164,7); 2,499(121,9); 2,494(59,5); 2,339(0,4); 2,335(0,8); 2,330(1,1); 2,326(0,8); 2,321(0,4); 1,398(1,6); 1,231(0,4); 0,000(1,0) 42 2,75 2,77 1H-NMR(601,6 MHz, CDCl3): δ = 9,251(2,6); 9,248(2,6); 8,710(1,9); 8,707(2,0); 8,702(2,0); 8,699(1,9); 8,320(1,3); 8,3174(1,7); 8,3167(1,6); 8,314(1,3); 8,307(1,3); 8,304(1,7); 8,303(1,7); 8,301(1,3); 8,151(4,3); 8,136(4,6); 7,969(3,3); 7,965(3,5); 7,886(1,7); 7,882(1,6); 7,872(1,8); 7,868(1,7); 7,450(1,4); 7,449(1,4); 7,442(1,4); 7,441(1,4); 7,437(1,5); 7,436(1,5); 7,432(1,3); 7,429(1,4); 7,428(1,4); 7,280(2,5); 7,261(188,5); 7,085(1,1); 6,923(4,6); 6,913(2,7); 6,908(4,9); 3,488(1,4); 3,471(4,3); 3,455(4,6); 3,438(1,6); 2,379(16,0); 1,584(0,4); 1,558(335,1); 1,530(0,4); 1,284(0,4); 1,254(3,2); 0,880(0,5); 0,005(0,8); 0,000(25,5); -0,006(0,9) Examples 1-4 are not included in the scope of protection and are to be regarded as comparative examples. <b><u> Table 2 </ u></b> Analytical data for the specified compounds. Expl logP [a] logP [b] 1 H-NMR [σ (ppm)] or LC-MS [m / z] 1 4.81 4.75 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.366 (9.6); 9,331 (9.4); 9,330 (9.2); 8.819 (7.7); 8.815 (8.5); 8,807 (8.3); 8.803 (8.5); 8,615 (14.3); 8,593 (16.0); 8,536 (4.4); 8.532 (5.7); 8,530 (5.6); 8,526 (4.5); 8,516 (4.8); 8,512 (5.8); 8.510 (6.2); 8,506 (4.6); 8,318 (0.8); 8,208 (9.7); 8,188 (9.7); 8,040 (6.9); 8,036 (7.9); 8,018 (7.2); 8,014 (6.9); 7,685 (5.6); 7,683 (5.7); 7,673 (5.4); 7,671 (5.5); 7,665 (5.4); 7,663 (5.4); 7,653 (5.3); 7,651 (5.4); 7,423 (8.2); 7,411 (0.5); 7,392 (8.1); 4,008 (4.2); 3,982 (13.4); 3,956 (14.0); 3,930 (4.8); 3.330 (261.5); 2,682 (0.7); 2,677 (1.5); 2,673 (2.1); 2,668 (1.6); 2,664 (0.8); 2,656 (0.3); 2,526 (5.6); 2,521 (8.5); 2.512 (114.8); 2,508 (235.5); 2.504 (315.5); 2.499 (263.2); 2,420 (1.4); 2,368 (0.5); 2,335 (1.8); 2,330 (2.1); 2,326 (1.6); 2,321 (0.9); 1,990 (0.6); 1,398 (4.1); 0.146 (2.5); 0.029 (0.4); 0.008 (19.6); 0.000 (555.1); -0.009 (21.4); -0.033 (0.4); -0.150 (2.6). 2 4.67 4.64 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.322 (1.9); 8.808 (1.4); 8.799 (1.4); 8,591 (4.3); 8,581 (0.4); 8.569 (5.1); 8,560 (0.4); 8,516 (1.3); 8,511 (1.9); 8.507 (1.4); 8,496 (1.4); 8,491 (2.0); 8,487 (1.4); 8,317 (0.5); 8,307 (3.9); 8.301 (7.3); 8,279 (4.2); 8,070 (2.2); 8,066 (2.1); 8,050 (2.2); 8,046 (2.2); 7,677 (1.7); 7,666 (1.7); 7,658 (1.6); 7,646 (1.6); 7,456 (3.0); 7,436 (2.8); 4,156 (1.3); 4,130 (4.2); 4,104 (4.4); 4,078 (1.5); 3,331 (95.2); 2,677 (0.4); 2,673 (0.6); 2,668 (0.5); 2,526 (1.4); 2,512 (35.3); 2,508 (70.8); 2,504 (93.0); 2,499 (68.9); 2,495 (34.7); 2.455 (16.0); 2,391 (0.8); 2,340 (0.4); 2,335 (0.5); 2,330 (0.7); 2,326 (0.5); 1,397 (3.2); 0.008 (0.4); 0,000 (11.3); -0.008 (0.5). 3 3.02 3.09 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.341 (3.3); 9,336 (3.3); 8.823 (2.3); 8,820 (2.6); 8,811 (2.5); 8.808 (2.6); 8,654 (3.6); 8.633 (4.0); 8,593 (0.4); 8,581 (3.0); 8.562 (3.0); 8,535 (2.0); 8,530 (1.5); 8,519 (1.5); 8,514 (2.0); 8.510 (1.5); 8,317 (0.4); 8,126 (2.1); 8,122 (2.4); 8,104 (2.1); 8,101 (2.1); 7,687 (1.8); 7,675 (1.9); 7,667 (1.8); 7.655 (1.7); 7,526 (2.5); 7,496 (2.5); 5,757 (2.9); 4,261 (0.4); 4,251 (0.6); 4,232 (1.0); 4,224 (1.7); 4,205 (1.9); 4,197 (1.9); 4,178 (1.7); 4,169 (1.0); 4,150 (0.6); 4,141 (0.4); 3,329 (81.5); 2,672 (1.0); 2,668 (0.8); 2.507 (113.6); 2.503 (144.6); 2.499 (114.9); 2,468 (16.0); 2,429 (0.4); 2,330 (1.0); 0,000 (17.6). 4 2.99 2.98 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.325 (3.3); 9,320 (3.3); 8,813 (2.4); 8,810 (2.6); 8,802 (2.5); 8,798 (2.6); 8.717 (4.0); 8,713 (4.2); 8,629 (3.7); 8,607 (4.3); 8,522 (1.4); 8,517 (2.0); 8,512 (1.5); 8,502 (1.5); 8,497 (2.1); 8.492 (1.4); 8,338 (2.3); 8,331 (5.1); 8,318 (2.6); 8.310 (4.1); 7,680 (1.8); 7.668 (1.8); 7,660 (1.8); 7,648 (1.7); 7,552 (2.9); 7,532 (2.8); 5,758 (0.9); 4,235 (0.7); 4,226 (0.7); 4,208 (2.0); 4,199 (1.9); 4,181 (2.0); 4,172 (2.0); 4,154 (0.7); 4,145 (0.7); 4,136 (0.3); 3,366 (0.3); 3,331 (76.2); 2,672 (0.7); 2,507 (78.8); 2.503 (100.7); 2,499 (78.2); 2,460 (16.0); 2,330 (0.7); 0,000 (2.6). 6 2.53 2.97 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.151 (5.5); 9,147 (5.6); 8,683 (3.9); 8,679 (4.2); 8,671 (4.1); 8,667 (4.1); 8,335 (0.5); 8,327 (2.5); 8.323 (3.4); 8,318 (2.6); 8.314 (1.6); 8,307 (2.7); 8,302 (3.5); 8,298 (2.5); 8,140 (8.2); 8,118 (8.6); 7,580 (3.1); 7,569 (3.1); 7,561 (3.1); 7,549 (2.9); 7.521 (0.4); 6,731 (7.9); 6,708 (7.7); 5,754 (1.8); 3,510 (5.5); 3,494 (14.2); 3,477 (5.8); 3.316 (134.8); 3,141 (0.9); 2,675 (1.7); 2,671 (2.3); 2,666 (1.7); 2,632 (1.8); 2,571 (0.4); 2,567 (0.4); 2,562 (0.4); 2,524 (7.4); 2,510 (135.4); 2.506 (268.7); 2.502 (352.7); 2.497 (264.6); 2,493 (136.1); 2,333 (1.6); 2,328 (2.2); 2,324 (1.7); 2,018 (0.7); 2,003 (6.0); 1,993 (7.0); 1,986 (16.0); 1,980 (7.3); 1,970 (5.9); 1.335 (0.8); 1,259 (0.7); 1,250 (0.6); 1,233 (2.1); 0.854 (0.4); 0.146 (2.1); 0.031 (0.4); 0.022 (0.8); 0.008 (17.8); 0.000 (454.2); -0.008 (23.0); -0.028 (0.7); -0.150 (2,2). 7 1.43 1.50 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.357 (3.1); 9,352 (3.1); 9.049 (8.9); 9,037 (9.0); 8.829 (2.3); 8,825 (2.5); 8.817 (2.4); 8,813 (2.4); 8,667 (16.0); 8,564 (1.3); 8,560 (1.9); 8.555 (1.4); 8.544 (1.4); 8,539 (1.9); 8,535 (1.3); 8,319 (0.7); 7,690 (1.7); 7,678 (1.7); 7,671 (1.7); 7.659 (1.6); 7,634 (2.5); 7,622 (4.7); 7,610 (2.4); 5,759 (1.0); 3.330 (115.0); 2,676 (1.3); 2,672 (1.7); 2,667 (1.3); 2,525 (4.6); 2.507 (204.2); 2.503 (264.8); 2.498 (196.5); 2,334 (1.3); 2,329 (1.7); 2,325 (1.3); 1,258 (0.5); 1,233 (1.9); 0.852 (0.6); 0.833 (0.3); 0.146 (0.6); 0.008 (4.5); 0.000 (124.1); -0.150 (0.6). 8th 2.12 2.68 1 H-NMR (601.6 MHz, CDCl 3): δ = 9.345 (6.9); 9,344 (7.1); 9,342 (7.2); 9,341 (6.4); 8.772 (5.8); 8.769 (5.9); 8.764 (6.0); 8.762 (5.7); 8,737 (3.9); 8,736 (4.6); 8,734 (4.6); 8,733 (4.0); 8,729 (4.2); 8,728 (4.6); 8,727 (4.4); 8,725 (3.6); 8.648 (12.4); 8,634 (14.1); 8,511 (4.7); 8.510 (6.8); 8,508 (4.3); 8,498 (4.9); 8,497 (7.1); 8,495 (4.3); 8,426 (15.6); 8,422 (5.2); 8,421 (4.8); 8,418 (3.8); 8.412 (16.0); 8,409 (5.6); 8.408 (5.0); 8.405 (3.7); 7,883 (3.5); 7,880 (3.4); 7,870 (5.6); 7,868 (5.5); 7,857 (3.6); 7,854 (3.4); 7,498 (4.4); 7,496 (4.2); 7,490 (4.5); 7,488 (4.3); 7,484 (4.4); 7,483 (4.1); 7,477 (4.3); 7,475 (4.0); 7,434 (0.3); 7,369 (3.9); 7,368 (3.8); 7,362 (3.9); 7,360 (4.1); 7,357 (4.1); 7,355 (3.7); 7,349 (3.7); 7,347 (3.4); 7,262 (58.9); 7,086 (0.3); 1.594 (59.7); 1.333 (0.7); 1,284 (1.0); 1,254 (1.5); 0.880 (0.3); 0.844 (0.4); 0.839 (0.4); 0.005 (1.5); 0,000 (45.7); -0.006 (1.7). 9 3.99 4.06 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.638 (3.9); 9,195 (2.9); 9.191 (3.0); 8.717 (2.3); 8,713 (2.4); 8.705 (2.4); 8.701 (2.4); 8,378 (1.2); 8,374 (1.7); 8,368 (1.3); 8,358 (1.4); 8,353 (1.8); 8.348 (1.4); 8,318 (0.4); 8,236 (4.2); 8,214 (4.5); 8,007 (3.2); 8.002 (3.3); 7,607 (1.7); 7,595 (1.6); 7,587 (1.6); 7.573 (2.1); 7,571 (2.0); 7,565 (1.7); 7,550 (2.0); 7,545 (2.0); 7,236 (2.9); 7.215 (2.5); 7,038 (4.0); 7.015 (4.0); 4,056 (0.4); 4,038 (1.1); 4,020 (1.1); 4,002 (0.4); 3,954 (1.2); 3,928 (3.7); 3,902 (3.9); 3,876 (1.3); 3.330 (134.6); 2,676 (0.8); 2,672 (1.1); 2,667 (0.8); 2,525 (3.4); 2,511 (66.4); 2.507 (131.9); 2.503 (172.2); 2.498 (126.1); 2,494 (63.2); 2,338 (16.0); 2,266 (0.5); 1,989 (4.8); 1,397 (0.4); 1.193 (1.3); 1.175 (2.5); 1,157 (1.3); 0.146 (0.9); 0.008 (7.6); 0.000 (197.5); -0.008 (8.7); -0.150 (0.9). 10 2.65 2.69 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.354 (8.2); 9,352 (8.9); 9,348 (8.9); 9,346 (8.5); 8.849 (7.2); 8,845 (7.8); 8,837 (7.7); 8.833 (7.7); 8.781 (8.4); 8,780 (8.4); 8,760 (9.1); 8.759 (9.0); 8.561 (4.4); 8,557 (5.5); 8,556 (5.3); 8,551 (4.4); 8,541 (4.8); 8,537 (5.5); 8,535 (5.8); 8,531 (4.5); 8,151 (16.0); 8,130 (15.0); 7,700 (5.4); 7.698 (5.5); 7.688 (5.2); 7.686 (5.3); 7,680 (5.2); 7,678 (5.2); 7.668 (5.1); 7,666 (5.1); 3.338 (38.7); 2,681 (0.3); 2,677 (0.5); 2,672 (0.3); 2,530 (1.2); 2,525 (1.7); 2,517 (26.2); 2,512 (54.4); 2,508 (72.0); 2,503 (51.8); 2,499 (24.7); 2,339 (0.3); 2,334 (0.5); 2,330 (0.3); 1,993 (0.4); 1,225 (1.4); 0.008 (0.9); 0,000 (30.6); -0.009 (1.0). 11 2.10 1.95 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.179 (5.8); 9,174 (5.8); 8,709 (4.1); 8,706 (4.4); 8.697 (4.3); 8.694 (4.2); 8.356 (3.6); 8,336 (3.7); 8,317 (0.4); 8.222 (6.4); 8,199 (6.7); 7.598 (3.3); 7,586 (3.4); 7,578 (3.3); 7,566 (3.0); 7,138 (6.3); 7,115 (6.1); 3,745 (9.6); 3,733 (16.0); 3,721 (13.6); 3,609 (13.4); 3,596 (15.7); 3,585 (9.5); 3.332 (188.8); 2,672 (1.2); 2.503 (168.0); 2,330 (1.1); 1,990 (0.5); 0,000 (15.6). 12 4.81 4.78 1 H-NMR (601.6 MHz, CDCl 3): δ = 9.227 (1.6); 9,224 (1.6); 8.677 (1.1); 8.674 (1.2); 8,669 (1.2); 8,666 (1.1); 8,297 (0.8); 8.293 (1.1); 8,290 (0.8); 8,283 (0.8); 8,280 (1.1); 8,277 (0.8); 7.901 (2.9); 7,885 (2.9); 7,424 (1.0); 7,423 (1.0); 7,413 (2.4); 7.410 (2.9); 7,403 (1.0); 7,402 (0.9); 7.310 (1.5); 7,296 (1.8); 7,264 (3.3); 7,164 (1.4); 7,160 (1.3); 7,151 (1.1); 7,147 (1.1); 6,627 (2.9); 6,611 (2.9); 5,299 (2.2); 3,545 (1.4); 3,538 (16.0); 3,438 (1.1); 3,422 (3.4); 3,406 (3.5); 3,391 (1.2); 2,491 (10.7); 2,442 (1.0); 2,359 (0.7); 1,688 (1.5); 1,254 (1.6); 0.000 (0.9). 13 3.82 3.72 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.397 (12.4); 9,334 (8.8); 9,330 (8.9); 8.819 (6.7); 8,816 (7.5); 8,807 (7.2); 8.804 (7.4); 8,747 (14.6); 8,725 (16.0); 8,538 (3.9); 8,533 (5.4); 8.528 (4.1); 8.518 (4.3); 8,512 (5.7); 8,508 (4.3); 8.382 (15.9); 8,317 (2.8); 8,235 (15.5); 8,213 (14.5); 7,992 (0.5); 7,684 (5.1); 7,682 (5.3); 7,672 (4.9); 7,670 (5.1); 7.664 (4.9); 7,662 (5.0); 7,652 (4.7); 7,650 (4.8); 3,329 (899.6); 2,676 (4.4); 2,672 (6.1); 2,667 (4.6); 2,542 (2.4); 2.525 (16.4); 2,520 (24.9); 2,511 (334.7); 2.507 (693.8); 2.503 (925.4); 2.498 (682.8); 2.494 (341.5); 2,334 (4.3); 2,329 (6.0); 2,325 (4.5); 2,075 (0.3); 1,148 (0.6); 0.146 (7.1); 0.032 (1.0); 0.025 (2.1); 0.008 (54.7); 0.000 (1562.0); -0.009 (65.0); -0.029 (1.5); -0.038 (0.8); -0.042 (0.6); -0.050 (0.5) - 0.065 (0.4); -0.150 (7.1). 14 1 H-NMR (400MHz, CDCl 3): δ = 9.23 (s, 1 H), 8.68 to 8.67 (m, 1 H), 8.29 to 8.26 (m, 1 H) , 8.12-8.09 (m, 1H), 7.43-7.40 (m, 1H), 6.96-6.94 (m, 1H), 5.25 (s, 1 H), 2.66 - 2.62 (m, 1H), 0.89 - 0.86 (m, 2H), 0.65 - 0.63 (m, 2H). 15 1.34 16 1 H-NMR (400MHz, CDCl 3): δ = 9.13 (s, 1 H), 8.77 to 8.76 (m, 1 H), 8.38 to 8.31 (m, 2 H) , 7.59 - 7.57 (m, 1H), 7.50 - 7.47 (m, 1H), 3.54 (s, 3H), 1.73 - 1.70 (m, 1 H), 1.18-1.14 (m, 2H), 0.84-0.80 (m, 2H). 17 1 H-NMR (400MHz, CDCl 3): δ = 9.29 (s, 1 H), 8.77 - 8.76 (m, 1 H), 8.39 - 8.32 (m, 2 H), 7 , 62-7.59 (m, 1H), 7.50-7.47 (m, 1H), 4.07-4.02 (m, 2H), 3.09 (s, 3H) , 1.26-1.22 (m, 3H). 18 1 H-NMR (400MHz, CDCl 3): δ = 9.14 (s, 1 H), 8.60 to 8.58 (m, 1 H), 8.21 to 8.18 (m, 1 H) , 7.94-7.92 (m, 1H), 7.38-7.32 (m, 1H), 6.48-6.46 (m, 1H), 4.64 (s, 1 H), 3.40-3.37 (m, 2H), 1.25-1.22 (m, 3H). 19 1 H-NMR (400MHz, CDCl 3): δ = 9.24 (s, 1 H), 8.70 to 8.69 (m, 1 H), 8.32 to 8.25 (m, 2 H) , 7.46-7.39 (m, 2H), 4.03-3.98 (m, 2H), 1.50-1.48 (m, 1H), 1.18-1.15 (m, 3H), 1.09 - 1.07 (m, 2H), 0.71 - 0.70 (m, 2H). 20 1.37 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.314 (2.4); 8,816 (1.7); 8,807 (1.8); 8,628 (5.0); 8,606 (5.4); 8.510 (1.6); 8,505 (2.4); 8,501 (1.8); 8,491 (1.9); 8,485 (2.6); 8.481 (1.9); 8.310 (0.4); 7,779 (5.8); 7.758 (5.6); 7,678 (1.8); 7,666 (1.9); 7,658 (1.9); 7,646 (1.8); 3,902 (16.0); 3,585 (1.0); 3,565 (0.9); 3,508 (0.5); 3,392 (22.5); 3.352 (536.8); 3,291 (2.1); 3,278 (2.7); 3.257 (2.4); 3,240 (1.3); 3,225 (3.3); 3,208 (2.3); 3,202 (2.9); 3,191 (2.2); 3,176 (1.8); 3,169 (1.5); 3,058 (0.9); 3,034 (1.2); 3,025 (0.9); 3,014 (1.1); 3,001 (1.0); 2,982 (0.7); 2,872 (0.5); 2,860 (0.5); 2,678 (1.0); 2,673 (1.3); 2,669 (1.0); 2,527 (3.5); 2,513 (74.3); 2.509 (156.7); 2.504 (219.6); 2,500 (164.1); 2,495 (78.1); 2,336 (1.0); 2.331 (1.4); 2,326 (1.1); 2,309 (0.5); 2,293 (0.9); 2,277 (1.1); 2,264 (0.9); 2,246 (1.2); 2,222 (1.5); 2,213 (0.5); 2,203 (1.4); 2,189 (0.8); 2,179 (0.7); 2,170 (0.7); 2.143 (0.9); 0.000 (3.0) 21 3.39 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.239 (2.3); 8.766 (1.5); 8,755 (1.6); 8,477 (2.7); 8.435 (12.4); 8,420 (1.8); 8.413 (1.9); 8,410 (2.2); 7,881 (1.3); 7,861 (1.5); 7,675 (1.5); 7.655 (3.0); 7,636 (1.9); 7,620 (1.2); 4,172 (16.0); 3,901 (7.5); 3,550 (0.8); 3,508 (0.7); 3.363 (521.7); 3.355 (877.8); 3,177 (0.8); 3,164 (0.8); 2,673 (1.5); 2.509 (170.4); 2.504 (235.5); 2,500 (187.4); 2.331 (1.3); 0.000 (2.2) 22 1.98 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.301 (1.3); 8,807 (0.9); 8,797 (0.9); 8,574 (2.8); 8,552 (3.0); 8,496 (0.9); 8,491 (1.5); 8,487 (0.9); 8,476 (0.9); 8,470 (1.4); 7.789 (2.5); 7,767 (2.4); 7,670 (0.9); 7,658 (1.0); 7,650 (1.0); 7.638 (0.9); 3,902 (2.8); 3,417 (0.4); 3,392 (13.0); 3.336 (158.8); 3,329 (84.5); 2,767 (1.4); 2,714 (10.8); 2,677 (0.5); 2,672 (0.6); 2,668 (0.4); 2,512 (34.0); 2,508 (69.0); 2,503 (95.5); 2,499 (72.2); 2,494 (35.4); 2,334 (0.4); 2,330 (0.5); 2,326 (0.4); 2,102 (2.6); 2,000 (16.0); 0.000 (1.7) 23 1.71 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.295 (2.6); 8.804 (1.8); 8.795 (1.8); 8,548 (6.3); 8,526 (6.8); 8,491 (1.7); 8.486 (2.5); 8.481 (1.8); 8,471 (1.8); 8,466 (2.6); 8.461 (1.7); 7.794 (5.6); 7.772 (5.4); 7.669 (1.9); 7,656 (1.9); 7.649 (1.9); 7,637 (1.8); 3,902 (4.8); 3,509 (0.4); 3,381 (33.0); 3,344 (337.1); 2,677 (0.7); 2,673 (1.0); 2,669 (0.7); 2,526 (2.7); 2,512 (56.7); 2,508 (118.3); 2.504 (166.3); 2.499 (127.2); 2,495 (63.3); 2,459 (2.0); 2,441 (6.0); 2,422 (6.1); 2,404 (2.0); 2,335 (0.7); 2.331 (0.9); 2,326 (0.7); 1,042 (7.8); 1,024 (16.0); 1.005 (7.4); 0.000 (1.1) 24 1.22 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.332 (1.3); 8,827 (0.9); 8.817 (0.9); 8,612 (3.9); 8,591 (4.1); 8,537 (0.9); 8.532 (1.1); 8.527 (0.9); 8,517 (0.9); 8,512 (1.2); 8.507 (0.8); 7,801 (4.0); 7,780 (3.8); 7,690 (0.9); 7,678 (0.9); 7,670 (0.9); 7,658 (0.8); 3,902 (2.5); 3,359 (205.8); 3,170 (0.6); 3,063 (14.1); 3,001 (16.0); 2,868 (1.7); 2,678 (0.3); 2,673 (0.5); 2,669 (0.4); 2,527 (1.3); 2,513 (28.2); 2,509 (59.8); 2,504 (84.0); 2,500 (62.4); 2,495 (29.6); 2,335 (0.3); 2.331 (0.5); 2,326 (0.4); 1.275 (0.6); 1,260 (1.1); 1.245 (0.9); 0.000 (1.3) 25 4.33 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 11.171 (13.2); 9.386 (7.1); 8,851 (4.9); 8,840 (5.0); 8.732 (13.9); 8,711 (16.0); 8,587 (3.8); 8.582 (5.8); 8,577 (4.4); 8,567 (4.2); 8.562 (6.0); 8,558 (4.4); 8.459 (11.7); 8,395 (15.4); 8,374 (14.2); 8,312 (0.5); 8,186 (5.6); 8,166 (6.1); 7,708 (4.6); 7,696 (4.7); 7.688 (4.7); 7.676 (4.2); 7,586 (5.2); 7,566 (11.4); 7,546 (7.8); 7,496 (8.3); 7,477 (5.1); 4,100 (0.3); 3,902 (14.2); 3,762 (0.3); 3,722 (0.4); 3,711 (0.4); 3,698 (0.4); 3,688 (0.4); 3,657 (0.5); 3,638 (0.5); 3,600 (0.6); 3,569 (0.7); 3,508 (1.4); 3.344 (1201.2); 3,216 (0.3); 3,176 (1.0); 3,164 (0.9); 2,678 (2.3); 2,673 (3.3); 2,669 (2.5); 2,623 (0.4); 2,612 (0.5); 2.509 (393.5); 2.504 (550.6); 2,500 (436.2); 2,335 (2.1); 2.331 (3.0); 2,326 (2.3); 1,249 (0.4); 1,232 (0.8); 0.000 (8.0) 26 2.09 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.358 (4.8); 9,308 (1.8); 9,292 (3.6); 9,276 (1.8); 8,840 (3.2); 8.829 (3.3); 8.677 (7.2); 8.655 (8.0); 8,558 (3.4); 8,537 (3.6); 8.293 (7.7); 8,271 (7.1); 7,696 (2.8); 7,684 (2.9); 7.676 (2.9); 7,665 (2.6); 3,902 (6.4); 3.835 (2.2); 3,818 (2.3); 3,800 (4.5); 3,784 (4.5); 3,765 (2.4); 3,749 (2.3); 3,608 (0.4); 3,540 (0.5); 3,508 (0.7); 3.347 (684.3); 3,171 (0.7); 2,674 (1.5); 2,580 (0.3); 2.509 (182.9); 2.504 (257.9); 2,500 (208.8); 2,335 (1.0); 2.331 (1.4); 2,327 (1.2); 2,282 (0.6); 1,700 (7.4); 1,653 (16.0); 1,605 (8.0); 1,208 (0.6); 1,191 (0.7); 0.000 (3.0) 27 1.39 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.344 (4.4); 8,830 (3.1); 8,820 (3.2); 8.621 (9.5); 8,600 (10.3); 8,536 (2.5); 8,531 (4.1); 8.527 (3.1); 8,516 (2.9); 8,511 (4.4); 8.507 (3.2); 8,259 (0.4); 7,856 (2.8); 7,835 (2.7); 7.688 (3.1); 7.676 (3.3); 7.668 (3.4); 7,656 (3.2); 4,563 (0.5); 3,902 (6.2); 3,705 (16.0); 3,510 (0.5); 3.343 (495.0); 3,170 (2.0); 2,991 (0.4); 2,869 (0.8); 2,857 (0.8); 2,678 (1.2); 2,673 (1.5); 2,669 (1.2); 2,526 (4.1); 2,513 (87.0); 2,508 (182.5); 2.504 (257.3); 2.499 (197.4); 2,335 (1.0); 2.331 (1.4); 2,326 (1.1); 0.000 (2.0) 28 2.17 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.640 (2.6); 9.624 (5.1); 9,607 (2.5); 9.363 (6.8); 8,843 (4.7); 8.833 (4.8); 8,689 (9.4); 8,668 (10.5); 8,563 (4.8); 8,543 (5.0); 8,303 (10.4); 8.282 (9.5); 7.698 (3.8); 7.686 (4.0); 7,679 (4.0); 7,666 (3.6); 4,167 (1.6); 4,144 (5.0); 4,127 (5.3); 4,120 (5.6); 4,103 (5.0); 4,079 (1.7); 3,902 (16.0); 3,511 (0.5); 3.337 (468.1); 3.332 (548.5); 3,170 (0.9); 2,672 (2.1); 2.503 (356.0); 2,330 (2.0); 1,234 (0.4); 0.000 (5.0) 29 2.23 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 8.801 (2.9); 8.436 (2.8); 8.413 (3.8); 8,392 (1.7); 7,965 (1.6); 7,945 (1.8); 7,902 (0.5); 7,889 (0.3); 7.711 (1.7); 7,692 (2.0); 7,634 (1.8); 7,623 (1.7); 7,614 (2.6); 7,588 (1.1); 7,560 (3.3); 7,527 (3.1); 7,518 (2.0); 7,505 (3.1); 7,499 (3.0); 7,480 (1.2); 3,902 (5.4); 3,550 (16.0); 3.330 (260.8); 3,269 (0.4); 3,176 (0.5); 3,163 (0.5); 2,672 (0.9); 2.503 (158.8); 2,330 (0.9); 0.000 (1.6) 30 1.25 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.299 (2.1); 9,295 (2.1); 8,802 (1.5); 8,792 (1.5); 8,595 (3.3); 8.573 (3.5); 8,499 (1.1); 8,494 (1.5); 8,489 (1.1); 8.479 (1.2); 8.474 (1.6); 8.469 (1.1); 7,819 (3.2); 7,797 (3.0); 7.669 (1.3); 7,657 (1.3); 7.649 (1.3); 7,637 (1.2); 3,902 (3.7); 3,431 (2.9); 3,423 (14.8); 3,414 (4.1); 3,394 (2.7); 3.330 (150.6); 3,176 (0.7); 3,163 (0.7); 2,991 (16.0); 2,931 (1.6); 2,912 (2.3); 2,893 (1.3); 2,676 (0.6); 2,672 (0.8); 2,667 (0.6); 2,525 (2.2); 2,511 (46.0); 2,507 (94.4); 2.502 (130.3); 2,498 (97.4); 2,494 (47.0); 2,334 (0.5); 2,329 (0.7); 2,325 (0.6); 0.000 (2.9) 31 1.54 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 8,800 (2.2); 8,444 (2.7); 8,422 (2.9); 8,406 (1.3); 8,391 (1.3); 7,965 (1.2); 7,945 (1.3); 7,864 (1.2); 7,844 (1.5); 7,778 (1.3); 7.759 (1.9); 7,722 (2.5); 7,687 (1.7); 7,667 (2.4); 7,648 (1.0); 7,624 (1.1); 7,607 (1.4); 7,588 (1.0); 7,550 (2.8); 7,528 (2.8); 4,110 (0.5); 4,098 (0.4); 3,902 (6.4); 3,565 (16.0); 3.348 (372.1); 3,268 (0.7); 3,176 (3.3); 3,164 (3.3); 2,673 (0.9); 2,669 (0.7); 2,512 (54.0); 2,508 (110.0); 2.504 (151.7); 2.499 (117.6); 2,495 (60.1); 2,335 (0.6); 2.331 (0.8); 2,326 (0.6); 0.000 (1.0) 32 1.35 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.353 (3.1); 9,023 (2.0); 9,011 (2.0); 8,837 (2.2); 8.829 (2.3); 8.647 (6.7); 8.625 (7.6); 8,547 (2.9); 8.527 (3.1); 8,258 (7.0); 8,236 (6.4); 7,691 (2.1); 7,680 (2.4); 7,672 (2.4); 7,660 (2.2); 3,903 (4.9); 3,339 (296.0); 3,171 (1.3); 2,992 (0.6); 2,869 (16.0); 2,857 (16.0); 2,673 (1.1); 2,543 (1.0); 2,508 (130.2); 2.504 (180.0); 2,500 (141.4); 2.331 (1.0); 1,232 (0.4); 1,214 (0.4); 0.000 (2.8) 33 1.53 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.332 (2.7); 8.829 (1.9); 8,820 (2.0); 8,608 (4.4); 8.588 (4.6); 8,586 (4.6); 8,529 (1.8); 8,524 (2.7); 8,520 (1.9); 8,509 (1.9); 8,504 (2.7); 8,500 (1.9); 7,792 (2.8); 7,782 (3.6); 7,771 (2.7); 7,761 (3.4); 7,685 (2.0); 7,673 (2.1); 7,666 (2.0); 7,654 (1.8); 3,902 (4.0); 3,558 (1.0); 3,540 (2.8); 3,522 (2.9); 3,504 (1.1); 3.340 (362.1); 3,310 (5.2); 3,292 (3.8); 3,274 (1.4); 3,029 (16.0); 2,970 (13.5); 2,869 (0.3); 2,857 (0.3); 2,678 (0.7); 2,673 (1.0); 2,669 (0.7); 2,508 (116.8); 2.504 (164.6); 2.499 (128.9); 2,335 (0.6); 2.331 (0.9); 2,326 (0.7); 1,202 (3.0); 1,184 (6.4); 1,167 (3.1); 1,154 (3.6); 1,137 (7.6); 1,119 (3.3); 0,000 (2.6) 34 2.10 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 11.355 (11.6); 9,384 (0.4); 8.957 (10.8); 8,936 (0.4); 8.848 (0.4); 8,768 (8.5); 8,746 (9.7); 8,719 (0.5); 8,644 (11.3); 8,564 (0.3); 8.473 (6.3); 8.457 (6.5); 8.419 (9.9); 8,397 (9.1); 8,312 (0.7); 8.293 (5.6); 8,272 (6.0); 8,111 (5.9); 8,091 (6.4); 7,900 (1.4); 7,755 (4.0); 7,735 (8.8); 7.715 (6.0); 7.689 (4.9); 7,671 (6.6); 7,650 (10.0); 7,629 (5.4); 7.567 (0.6); 7,546 (0.9); 7,527 (0.4); 4,105 (0.8); 4,095 (0.9); 3,902 (16.0); 3,716 (0.4); 3,704 (0.4); 3,676 (0.4); 3,662 (0.4); 3,623 (0.4); 3,554 (0.6); 3,542 (0.7); 3,509 (1.3); 3.340 (958.2); 3,213 (0.5); 3,177 (4.7); 3,163 (4.6); 2,673 (3.4); 2,633 (0.3); 2.503 (584.4); 2.331 (3.2); 1,233 (1.2); 0.852 (0.4); 0.831 (0.4); 0.000 (6.9) 35 2.03 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.352 (1.1); 9.166 (0.4); 9,152 (0.9); 9,137 (0.4); 8,837 (0.8); 8,827 (0.8); 8,659 (2.4); 8,638 (2.7); 8.555 (0.6); 8,550 (0.9); 8,545 (0.7); 8,535 (0.7); 8,530 (1.0); 8,525 (0.6); 8,272 (2.6); 8,251 (2.4); 7,693 (0.7); 7,681 (0.8); 7,673 (0.7); 7,661 (0.7); 3,902 (1.7); 3,565 (0.8); 3,549 (1.6); 3,530 (1.6); 3.514 (0.8); 3.346 (153.5); 2,724 (1.6); 2,705 (2.3); 2,688 (1.5); 2,678 (0.4); 2,673 (0.5); 2,669 (0.3); 2,543 (0.3); 2,526 (1.2); 2,513 (25.2); 2,508 (52.8); 2,504 (74.2); 2,499 (56.0); 2,495 (27.1); 2.331 (0.4); 2,116 (16.0); 0.000 (1.2) 36 3.09 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 11.332 (8.4); 11.193 (0.3); 9.382 (5.3); 8.849 (3.7); 8,839 (3.7); 8,760 (0.4); 8,739 (8.4); 8,718 (9.3); 8,646 (7.3); 8.583 (3.7); 8,563 (3.9); 8,454 (0.5); 8,404 (9.3); 8,382 (8.5); 8.310 (0.5); 8.293 (3.7); 8,272 (3.9); 7.757 (3.3); 7,737 (7.3); 7,717 (4.7); 7,708 (3.2); 7,696 (3.2); 7.688 (3.3); 7.676 (3.1); 7.649 (5.1); 7,630 (3.4); 3,902 (16.0); 3,706 (0.4); 3,509 (1.6); 3.357 (1127.4); 3,177 (1.2); 3,164 (1.1); 2,678 (1.6); 2,674 (2.2); 2.509 (269.0); 2.505 (368.5); 2.501 (284.8); 2,336 (1.5); 2,332 (2.0); 1,233 (1.1); 0.000 (3.9) 37 2.61 1 H NMR (601.6 MHz, d 6 -DMSO): δ = 11.548 (2.0); 8,828 (6.7); 8.826 (10.9); 8.824 (6.7); 8,585 (8.5); 8.570 (11.0); 8,467 (13.4); 8,452 (11.2); 8,409 (6.0); 8.408 (6.0); 8,407 (5.6); 8,400 (16.0); 8,397 (12.7); 8,291 (5.9); 8,280 (4.9); 8,278 (6.0); 8,275 (4.5); 7,996 (5.9); 7,982 (8.6); 7,981 (9.0); 7.966 (5.5); 7,735 (5.8); 7,722 (10.7); 7.709 (5.1); 7,632 (5.5); 7.621 (6.3); 7,619 (6.2); 7,608 (5.1); 3.321 (548.2); 2,617 (2.2); 2,614 (2.9); 2,611 (2.1); 2,523 (5.5); 2,520 (6.8); 2,517 (6.9); 2,508 (164.2); 2.505 (336.0); 2.502 (450.5); 2.499 (336.3); 2.496 (163.1); 2,389 (2.1); 2,386 (2.8); 2,383 (2.1); 1,233 (0.4); 0.000 (5.1) 38 1.18 1 H NMR (601.6 MHz, d 6 -DMSO): δ = 11.109 (2.1); 9,259 (2.2); 9.258 (2.3); 9,255 (2.3); 9.254 (2.2); 8,771 (1.9); 8,768 (2.0); 8.763 (2.0); 8,760 (2.0); 8,502 (3.5); 8,487 (4.3); 8.457 (1.1); 8,454 (1.4); 8,453 (1.3); 8,450 (1.1); 8,444 (1.2); 8,441 (1.4); 8,440 (1.5); 8,437 (1.1); 8,339 (1.1); 8,325 (0.9); 7.638 (1.3); 7,637 (1.3); 7,630 (1.3); 7,629 (1.3); 7,625 (1.4); 7,624 (1.3); 7,617 (1.3); 7,616 (1.3); 3,481 (1.8); 3,468 (3.6); 3,456 (2.1); 3.323 (117.5); 3,040 (16.0); 2,967 (1.8); 2,954 (3.0); 2,942 (1.7); 2,617 (0.4); 2,614 (0.5); 2,611 (0.4); 2,584 (0.6); 2,542 (0.9); 2,523 (0.9); 2,520 (1.1); 2,517 (1.1); 2,508 (28.3); 2,505 (59.2); 2,502 (80.0); 2,499 (58.9); 2,496 (27.9); 2,389 (0.4); 2,386 (0.5); 2,383 (0.4); 0.000 (1.1) 39 3.79 3.83 1 H-NMR (601.6 MHz, CDCl3): δ = 9.317 (0.8); 9.314 (0.8); 8.782 (0.6); 8,779 (0.6); 8,774 (0.6); 8,771 (0.6); 8.695 (0.7); 8.692 (0.8); 8,460 (1.3); 8,445 (1.5); 8,404 (0.4); 8.401 (0.5); 8.398 (0.4); 8,391 (0.4); 8,388 (0.5); 8,385 (0.4); 8,273 (1.5); 8,258 (1.3); 7,506 (0.5); 7,499 (0.5); 7,498 (0.5); 7.4934 (0.5); 7.4925 (0.5); 7.4854 (0.4); 7.4845 (0.4); 7,262 (15.5); 6,776 (1.0); 6,772 (1.0); 5,301 (0.5); 1.574 (20.4); 1,423 (0.5); 1.336 (0.5); 1.333 (0.5); 1,285 (1.2); 1,254 (16.0); 1,173 (0.4); 1,160 (0.3); 1,155 (0.3); 1,106 (0.5); 0.900 (0.4); 0.892 (1.1); 0.880 (1.6); 0.868 (1.0); 0.856 (0.6); 0.840 (1.1); 0.829 (0.9); 0.714 (0.4); 0.000 (3.6) 40 2.26 2.33 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.302 (6.3); 9,300 (7.0); 9,296 (6.9); 9,294 (6.7); 8,814 (6.0); 8,810 (6.6); 8,802 (6.4); 8,798 (6.5); 8,579 (15.0); 8,558 (15.8); 8,506 (3.9); 8,502 (4.6); 8,500 (4.6); 8,496 (3.9); 8.486 (4.1); 8,482 (4.6); 8,480 (5.0); 8,476 (3.9); 8,318 (0.5); 7,761 (16.0); 7,740 (15.1); 7,672 (4.6); 7,670 (4.9); 7,660 (4.5); 7,658 (4.7); 7,652 (4.4); 7,650 (4.6); 7,640 (4.3); 7.638 (4.5); 3,330 (93.2); 2,682 (0.4); 2,677 (0.8); 2,673 (1.1); 2,668 (0.8); 2,664 (0.4); 2,526 (2.7); 2,521 (4.0); 2,513 (58.2); 2,508 (121.6); 2.503 (164.7); 2.499 (121.9); 2,494 (59.5); 2,339 (0.4); 2,335 (0.8); 2,330 (1.1); 2,326 (0.8); 2,321 (0.4); 1,398 (1.6); 1,231 (0.4); 0.000 (1.0) 42 2.75 2.77 1 H-NMR (601.6 MHz, CDCl3): δ = 9.251 (2.6); 9,248 (2.6); 8.710 (1.9); 8.707 (2.0); 8,702 (2.0); 8.699 (1.9); 8,320 (1.3); 8.3174 (1.7); 8.3167 (1.6); 8.314 (1.3); 8,307 (1.3); 8,304 (1.7); 8,303 (1.7); 8.301 (1.3); 8,151 (4.3); 8,136 (4.6); 7,969 (3.3); 7,965 (3.5); 7,886 (1.7); 7,882 (1.6); 7,872 (1.8); 7,868 (1.7); 7,450 (1.4); 7,449 (1.4); 7.442 (1.4); 7,441 (1.4); 7,437 (1.5); 7,436 (1.5); 7,432 (1.3); 7.429 (1.4); 7.428 (1.4); 7,280 (2.5); 7,261 (188.5); 7,085 (1.1); 6,923 (4.6); 6,913 (2.7); 6,908 (4.9); 3,488 (1.4); 3,471 (4.3); 3,455 (4.6); 3,438 (1.6); 2,379 (16.0); 1,584 (0.4); 1.558 (335.1); 1,530 (0.4); 1,284 (0.4); 1,254 (3.2); 0.880 (0.5); 0.005 (0.8); 0,000 (25.5); -0.006 (0.9)

Biologische BeispieleBiological examples Myzus persicae - SprühtestMyzus persicae - spray test

Lösungsmittel:Solvent: 7878 Gewichtsteile AcetonParts by weight acetone 1,51.5 Gewichtsteile DimethylformamidParts by weight of dimethylformamide Emulgator:emulsifier: AlkylarylpolyglykoletherAlkylarylpolyglykolether

Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung löst man 1 Gewichtsteil Wirkstoff mit den angegebenen Gewichtsteilen Lösungsmittel und füllt mit Wasser, welches eine Emulgatorkonzentration von 1000 ppm enthält, bis zum Erreichen der gewünschten Konzentration auf. Zur Herstellung weiterer Testkonzentrationen wird mit emulgatorhaltigem Wasser verdünnt.To prepare a suitable preparation of active compound, 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water.

Chinakohlblattscheiben (Brassica pekinensis), die von allen Stadien der Grünen Pfirsichblattlaus (Myzus persicae) befallen sind, werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt.Chinese cabbage leaf discs ( Brassica pekinensis ) infested with all stages of the green peach aphid ( Myzus persicae ) are sprayed with an active compound preparation of the desired concentration.

Nach 6 Tagen wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle Blattläuse abgetötet wurden; 0 % bedeutet, dass keine Blattläuse abgetötet wurden.After 6 days, the effect is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.

Bei diesem Test zeigten z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 100 % bei einer Aufwandmenge von 500 g/ha: 1, 5, 24, 25, 26, 27, 29In this test, z. Example, the following compounds of the preparation examples effect of 100% at a rate of 500 g / ha: 1, 5, 24, 25, 26, 27, 29th

Bei diesem Test zeigten z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 90 % bei einer Aufwandmenge von 500 g/ha: 2, 4, 11, 12, 20, 22, 28, 30, 31, 35, 41In this test, z. Example, the following compounds of the preparation examples effect of 90% at a rate of 500 g / ha: 2, 4, 11, 12, 20, 22, 28, 30, 31, 35, 41st

Tetranychus urticae - Sprühtest, OP-resistentTetranychus urticae - spray test, op-resistant

Lösungsmittel:Solvent: 78,078.0 GewichtsteileAcetonParts by weight of acetone 1,51.5 Gewichtsteile DimethylformamidParts by weight of dimethylformamide Emulgator:emulsifier: AlkylarylpolyglykoletherAlkylarylpolyglykolether

Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung löst man 1 Gewichtsteil Wirkstoff mit den angegebenen Gewichtsteilen Lösungsmittel und füllt mit Wasser, welches eine Emulgatorkonzentration von 1000 ppm enthält, bis zum Erreichen der gewünschten Konzentration auf. Zur Herstellung weiterer Testkonzentrationen wird mit emulgatorhaltigem Wasser verdünnt.To prepare a suitable preparation of active compound, 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water.

Bohnenblattscheiben (Phaseolus vulgaris), die von allen Stadien der Gemeinen Spinnmilbe (Tetranychus urticae) befallen sind, werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt.Bean leaf discs (Phaseolus vulgaris) infected by all stages of the common spider mite (Tetranychus urticae) are sprayed with an active compound preparation of the desired concentration.

Nach 6 Tagen wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle Spinnmilben abgetötet wurden; 0 % bedeutet, dass keine Spinnmilben abgetötet wurden.After 6 days, the effect is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed.

Bei diesem Test zeigten z. B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 90 % bei einer Aufwandmenge von 500 g/ha: 9, 10In this test, z. For example, the following compounds of the preparation examples have an effect of 90% at a rate of 500 g / ha: 9, 10

Myzus persicae - Sprühtest Myzus persicae - spray test

Lösungsmittel:Solvent: 7 Gewichtsteile Dimethylformamid7 parts by weight of dimethylformamide Emulgator:emulsifier: AlkylarylpolyglykoletherAlkylarylpolyglykolether

Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung löst man 1 Gewichtsteil Wirkstoff mit den angegebenen Gewichtsteilen Lösungsmittel und füllt mit Wasser, welches eine Emulgatorkonzentration von 1000 ppm enthält, bis zum Erreichen der gewünschten Konzentration auf. Zur Herstellung weiterer Testkonzentrationen wird mit emulgatorhaltigem Wasser verdünnt. Bei erforderlicher Zugabe von Ammoniumsalzen oder/und Penetrationsförderern werden diese jeweils in einer Konzentration von 1000 ppm der Präparatelösung zugefügt.To prepare a suitable preparation of active compound, 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water. When necessary addition of ammonium salts or / and penetration promoters they are added in each case in a concentration of 1000 ppm of the preparation solution.

Paprikapflanzen (Capsicum annuum), die stark von der Grünen Pfirsichblattlaus (Myzus persicae) befallen sind, werden durch Sprühen mit der Wirkstoffzubereitung in der gewünschten Konzentration behandelt.Paprika plants ( Capsicum annuum ) which are heavily infested with the green peach aphid ( Myzus persicae ) are treated by spraying with the preparation of active compound in the desired concentration.

Nach 6 Tagen wird die Abtötung in % bestimmt. Dabei bedeutet 100 %, dass alle Läuse abgetötet wurden; 0 % bedeutet, dass keine Läuse abgetötet wurden.After 6 days the kill is determined in%. 100% means that all lice have been killed; 0% means that no lice have been killed.

Bei diesem Test zeigten z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 95 % bei einer Aufwandmenge von 100 ppm: 6
Bei diesem Test zeigten z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 100 % bei einer Aufwandmenge von 4 ppm: 1,2
Bei diesem Test zeigten z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 97 % bei einer Aufwandmenge von 4 ppm: 3
Bei diesem Test zeigten z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 95 % bei einer Aufwandmenge von 4 ppm: 4
Bei diesem Test zeigten z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 80 % bei einer Aufwandmenge von 4 ppm: 8In this test, z. Example, the following compounds of the preparation examples effect of 95% at a rate of 100 ppm: 6
In this test, z. Example, the following compounds of the preparation examples effect of 100% at an application rate of 4 ppm: 1.2
In this test, z. Example, the following compounds of the preparation examples effect of 97% at an application rate of 4 ppm: 3
In this test, z. Example, the following compounds of the preparation examples effect of 95% at a rate of 4 ppm: 4
In this test, z. Example, the following compounds of the preparation examples effect of 80% at a rate of 4 ppm: 8

Aphis gossypii - Sprühtest Aphis gossypii - spray test

Lösungsmittel:Solvent: 7 Gewichtsteile Dimethylformamid7 parts by weight of dimethylformamide Emulgator:emulsifier: AlkylarylpolyglykoletherAlkylarylpolyglykolether

Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung löst man 1 Gewichtsteil Wirkstoff mit den angegebenen Gewichtsteilen Lösungsmittel und füllt mit Wasser, welches eine Emulgatorkonzentration von 1000 ppm enthält, bis zum Erreichen der gewünschten Konzentration auf. Zur Herstellung weiterer Testkonzentrationen wird mit emulgatorhaltigem Wasser verdünnt. Bei erforderlicher Zugabe von Ammoniumsalzen oder/und Penetrationsförderern werden diese jeweils in einer Konzentration von 1000 ppm der Präparatelösung zugefügt.To prepare a suitable preparation of active compound, 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water. When necessary addition of ammonium salts or / and penetration promoters they are added in each case in a concentration of 1000 ppm of the preparation solution.

Baumwollpflanzen (Gossypium hirsutum), die stark von der Baumwollblattlaus (Aphis gossypii) befallen sind, werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt.Cotton plants ( Gossypium hirsutum ) which are heavily attacked by the cotton aphid ( Aphis gossypii ) are sprayed with an active compound preparation of the desired concentration.

Nach 6 Tagen wird die Abtötung in % bestimmt. Dabei bedeutet 100 %, dass alle Blattläuse abgetötet wurden; 0 % bedeutet, dass keine Blattläuse abgetötet wurden.After 6 days the kill is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.

Bei diesem Test zeigte z. B. die folgende Verbindungen der Herstellungsbeispiele Wirkung von 80 % bei einer Aufwandmenge von 4 ppm: 7, 24In this test, z. Example, the following compounds of the preparation examples effect of 80% at a rate of 4 ppm: 7, 24

Claims (5)

  1. Compounds of the formula (I)
    Figure imgb0463
     in which
    A represents an A radical from the group consisting of (A-b) to (A-f)
    Figure imgb0464
     where the broken line denotes the bond to the carbon atom of the bicyclic system of the formula (I) and
    B2 represents a radical from the group consisting of hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy and in each case optionally substituted cycloalkyl and cycloalkenyl,
    Q represents oxygen or sulfur,
    R1 represents a radical from the group consisting of hydrogen, alkyl, alkoxy and cyano,
    R2 a) represents a B radical from the group consisting of
    Figure imgb0465
    Figure imgb0466
    Figure imgb0467
    Figure imgb0468
    Figure imgb0469
    Figure imgb0470
    Figure imgb0471
    Figure imgb0472
    Figure imgb0473
     where the broken line denotes the bond to the carbon atom of the bicyclic system of the formula (I), or
    R2 b) represents a D radical from the group consisting of (D-1) to (D-3)
    Figure imgb0474
     where the broken line denotes the bond to the carbon atom of the bicyclic system of the formula (I), or
    R2 c) represents a radical of the formula
    Figure imgb0475
     where the broken line denotes the bond to the carbon atom of the bicyclic system of the formula (I), or
    R2 d) represents a radical of the formula
    Figure imgb0476
     where the broken line denotes the bond to the carbon atom of the bicyclic system of the formula (I), or
    R2 e) represents an F radical from the group consisting of (F-1) to (F-11)
    Figure imgb0477
    Figure imgb0478
    Figure imgb0479
    Figure imgb0480
     where the broken line denotes the bond to the carbon atom of the bicyclic system of the formula (I), or
    R2 f) represents a radical from the group consisting of haloalkyl and carboxyl,
    R2 g) represents a radical of the formula
    Figure imgb0481
     where the broken line denotes the bond to the carbon atom of the bicyclic system of the formula (I), in which
    G2 represents hydrogen or a radical from the group consisting of halogen, nitro, amino, cyano, alkylamino, haloalkylamino, dialkylamino, alkyl, haloalkyl, saturated or unsaturated cycloalkyl which is optionally substituted and optionally interrupted by one or more heteroatoms, cycloalkylalkyl, alkoxy, haloalkoxy, alkoxyalkyl, halogenated alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, bis(alkoxy)alkyl, bis(haloalkoxy)alkyl, alkoxy(alkylsulfanyl)alkyl, alkoxy(alkylsulfinyl)alkyl, alkoxy(alkylsulfonyl)alkyl, bis(alkylsulfanyl)alkyl, bis(haloalkylsulfanyl)alkyl, bis(hydroxyalkylsulfanyl)alkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alpha-hydroxyiminoalkoxycarbonylalkyl, alpha-alkoxyiminoalkoxycarbonylalkyl, C(X2)NR3R4, NR6R7, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, the heterocyclyl radicals dioxanyl, dioxolanyl, dioxepanyl, dioxocanyl, oxathianyl, oxathiolanyl, oxathiepanyl, oxathiocanyl, dithianyl, dithiolanyl, dithiepanyl, dithiocanyl, oxathianyl oxide, oxathiolanyl oxide, oxathiepanyl oxide, oxathiocanyl oxide, oxathianyl dioxide, oxathiolanyl dioxide, oxathiepanyl dioxide, oxathiocanyl dioxide, morpholinyl, triazolinonyl, oxazolinyl, dihydrooxadiazinyl, dihydrodioxazinyl, dihydrooxazolyl, dihydrooxazinyl and pyrazolinonyl (which for their part may be substituted by alkyl, haloalkyl, alkoxy and alkoxyalkyl), phenyl (which for its part may be substituted by halogen, cyano, nitro, alkyl and haloalkyl), the heteroaryl radicals pyridyl, pyridyl N-oxide, pyrimidyl, imidazolyl, pyrazolyl, oxazolyl, thiazolyl, furanyl, thienyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyrazinyl, triazinyl, tetrazinyl and isoquinolinyl (which for their part may be substituted by halogen, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxyalkyl, alkylthio, alkylthioalkyl and cycloalkyl) and the heteroarylalkyl radicals triazolylalkyl, pyridylalkyl, pyrimidylalkyl and oxadiazolylalkyl (which for their part may be substituted by halogen and alkyl),
    or
    G2 represents a C radical from the group consisting of (C-1) to (C-9)
    Figure imgb0482
    Figure imgb0483
    Figure imgb0484
     where the broken line denotes the bond to the B radicals,
    X represents oxygen or sulfur,
    X represents oxygen or sulfur,
    X1 represents a radical from the group consisting of hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, cycloalkyl, alkoxy and haloalkoxy,
    X2 represents oxygen, sulfur, NR5 or NOH,
    L represents oxygen or sulfur,
    V-Z represents R24CH-CHR25 or R24C=CR25,
    n represents 1 or 2,
    m represents 1, 2, 3 or 4,
    R represents NR18R19, or represents an in each case optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, alkoxyalkyl, alkyl-S-alkyl, alkyl-S(O)-alkyl, alkyl-S(O)2-alkyl, R18-CO-alkyl, NR18R19-CO-alkyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, phenyl, phenylalkyl, hetaryl and hetarylalkyl,
    R3 represents hydrogen or alkyl,
    R4 represents a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, aryl, arylalkyl and hetarylalkyl,
    R5 represents a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, aryl, arylalkyl and hetarylalkyl, or
    R3 and R4 together with the nitrogen atom to which they are attached form a ring which may contain one or more further heteroatoms from the group consisting of nitrogen, oxygen and sulfur, or
    R3 and R5 together with the nitrogen atoms to which they are attached form a ring,
    R6 represents hydrogen or alkyl,
    R7 represents a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy, haloalkoxy, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, aryl, arylalkyl and hetarylalkyl, or
    R6 and R7 together with the nitrogen atom to which they are attached form a ring which may contain one or more further heteroatoms from the group consisting of nitrogen, oxygen and sulfur,
    R8 represents a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkoxy, haloalkoxy, alkenyl, alkoxyalkyl, in each case optionally halogen-substituted alkylcarbonyl and alkylsulfonyl, optionally halogen-substituted alkoxycarbonyl, optionally halogen-, alkyl-, alkoxy-, haloalkyl- and cyano-substituted cycloalkylcarbonyl, or a cation, or an optionally alkyl- or arylalkyl-substituted ammonium ion,
    R9 represents a radical from the group consisting of in each case optionally substituted alkyl, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings may contain at least one heteroatom from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen, in each case optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group,
    R8 and R9 in the radicals (C-1) and (F-1), together with the N-S(O)n group to which they are attached, may also form a saturated or unsaturated and optionally substituted 4- to 8-membered ring which may contain one or more further heteroatoms from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen and/or at least one carbonyl group,
    R10 represents hydrogen or alkyl,
    R8 and R10 in the radicals (C-2) and (F-2), together with the nitrogen atoms to which they are attached, may also be a saturated or unsaturated and optionally substituted 4- to 8-membered ring which may contain at least one further heteroatom from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen and/or at least one carbonyl group,
    R9 and R10 in the radicals (C-2) and (F-2) may also form, together with the N-S(O)n group to which they are attached, a saturated or unsaturated and optionally substituted 4- to 8-membered ring which may contain one or more further heteroatoms from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen and/or at least one carbonyl group,
    R11 represents an in each case optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyl, cycloalkyloxy, cycloalkenyloxy, cycloalkylalkoxy, alkylthio, alkenylthio, phenoxy, phenylthio, benzyloxy, benzylthio, heteroaryloxy, heteroarylthio, heteroarylalkoxy and heteroarylalkylthio,
    R12 represents an in each case optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyl, cycloalkyloxy, cycloalkenyloxy, cycloalkylalkoxy, alkylthio, alkenylthio, phenoxy, phenylthio, benzyloxy, benzylthio, heteroaryloxy, heteroarylthio, heteroarylalkoxy and heteroarylalkylthio,
    R11 and R12 in the radicals (C-3) and (F-3) may also form, together with the phosphorus atom to which they are bonded, a saturated or unsaturated and optionally substituted 5- to 7-membered ring which may contain one or two heteroatoms from the group consisting of oxygen (where oxygen atoms must not be immediately adjacent to one another) and sulfur,
    R13 represents an in each case optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, phenyl and phenylalkyl,
    R14 represents an in each case optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, phenyl and phenylalkyl,
    R15 represents a radical from the group consisting of in each case optionally substituted alkyl, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings may contain at least one heteroatom from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen, in each case optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group,
    R8 and R15 in the radicals (C-6) and (F-6) may also form, together with the N-S(O)n group to which they are attached, a saturated or unsaturated and optionally substituted 4- to 8-membered ring which may contain one or more further heteroatoms from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen and/or at least one carbonyl group,
    R16 represents a radical from the group consisting of hydrogen, in each case optionally substituted alkyl, alkoxy, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings may contain at least one heteroatom from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen, in each case optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group,
    R8 and R16 in the radicals (C-7) and (F-7) may also form, together with the nitrogen atom to which they are attached, a saturated or unsaturated and optionally substituted 4- to 8-membered ring which may contain one or more further heteroatoms from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen and/or at least one carbonyl group,
    R17 represents a radical from the group consisting of in each case optionally substituted alkyl, alkoxy, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings may contain at least one heteroatom from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen, in each case optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group,
    R8 and R17 in the radicals (C-8) and (F-8) may also form, together with the N-C(X) group to which they are attached, a saturated or unsaturated and optionally substituted 4- to 8-membered ring which may contain one or more further heteroatoms from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen and/or at least one carbonyl group,
    R18 represents a radical from the group consisting of hydrogen, hydroxy, in each case optionally substituted alkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkylcarbonyl, alkoxycarbonyl, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl, cycloalkenyl and cycloalkenylalkyl, in which the rings may contain at least one heteroatom from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen, in each case optionally substituted aryl, arylalkyl, heteroaryl and heteroarylalkyl and an optionally substituted amino group,
    R19 represents a radical from the group consisting of hydrogen, represents an alkali metal or alkaline earth metal ion or represents an ammonium ion which is optionally mono- to tetrasubstituted by C1-C4-alkyl or represents an in each case optionally halogen- or cyano-substituted radical from the group consisting of alkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl and alkylsulfonylalkyl,
    Y1 and Y2 independently of one another represent C=O or S(O)2,
    Y3 represents a radical from the group consisting of hydrogen, halogen, cyano, alkyl, cycloalkyl, haloalkyl, alkoxy, haloalkoxy and NR20R21,
    W represents a radical from the group consisting of O, S, SO and SO2,
    R22 represents a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, optionally halogen-substituted alkoxyalkyl, optionally halogen-substituted bis(alkoxy)alkyl, optionally halogen-substituted alkylsulfanylalkyl, optionally halogen-substituted alkylcarbonylalkyl, optionally halogen-substituted alkylsulfinylalkyl, optionally halogen-substituted alkylsulfonylalkyl, dialkylaminosulfanylalkyl, dialkylaminosulfinylalkyl, dialkylaminosulfonylalkyl, optionally halogen-substituted alkoxycarbonyl, optionally halogen-substituted alkoxycarbonylalkyl, optionally halogen-substituted alkynyloxy, optionally halogen-substituted alkynyloxycarbonyl, dialkylaminocarbonyl, N-alkyl-N-cycloalkylaminocarbonyl, dialkylaminocarbonylalkyl, N-alkyl-N-cycloalkylaminocarbonylalkyl, heterocyclylcarbonylalkyl, alkylsulfanyl, haloalkylsulfanyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, cycloalkyl which is optionally substituted by halogen, cyano, nitro, alkyl, cycloalkyl, haloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, haloalkoxycarbonyl or hetaryl (which for its part is optionally substituted by alkyl or halogen), cycloalkylcarbonyl which is optionally substituted by halogen, cyano, nitro, alkyl, haloalkyl, cycloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, haloalkoxycarbonyl or hetaryl (which for its part is optionally substituted by alkyl or halogen), cycloalkylalkyl which is optionally substituted by halogen, cyano, nitro, alkyl, haloalkyl, cycloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, haloalkoxycarbonyl or hetaryl (which for its part is optionally substituted by alkyl or halogen), optionally substituted heterocyclyl, heterocyclylalkyl which is optionally substituted by halogen, cyano (also in the alkyl moiety), nitro, hydroxy, alkyl, haloalkyl, cycloalkyl (which is optionally substituted), alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, amino, alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonylamino, alkoxyalkyl, haloalkoxyalkyl, alkenyl, alkynyl, cycloalkylalkyl, alkylcarbonyl, alkoxycarbonyl or aminocarbonyl, aryl which is optionally substituted by halogen, cyano, nitro, hydroxy, amino, alkyl, haloalkyl, cycloalkyl (which is optionally substituted), alkoxy or haloalkoxy, arylalkyl which is optionally substituted by halogen, cyano (also in the alkyl moiety), nitro, hydroxy, amino, alkyl, cycloalkyl (which is optionally substituted), haloalkyl, alkoxy or haloalkoxy, hetarylalkyl which is optionally substituted by halogen, cyano (also in the alkyl moiety), nitro, hydroxy, alkyl, haloalkyl, cycloalkyl (which is optionally substituted), alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, amino, alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonylamino, alkoxyalkyl, haloalkoxyalkyl, alkenyl, alkynyl, cycloalkylalkyl, alkylcarbonyl, alkoxycarbonyl or aminocarbonyl, or
    R22 represents a D radical from the group consisting of (D-1) to (D-3)
    Figure imgb0485
     an E radical from the group consisting of (E-1) to (E-11)
    Figure imgb0486
    Figure imgb0487
    Figure imgb0488
     of the group consisting of (E-18) to (E-51)
    Figure imgb0489
    Figure imgb0490
    Figure imgb0491
    Figure imgb0492
    Figure imgb0493
    Figure imgb0494
    Figure imgb0495
    Figure imgb0496
    Figure imgb0497
    Figure imgb0498
     or
    in the case R2 = d),
    R22 also represents an E radical from the group consisting of E-12 to E-17
    Figure imgb0499
    Figure imgb0500
     where here and below, the broken line denotes the bond to the appropriate atom in the radicals c), d) and g),
    R20 represents a radical from the group consisting of hydrogen, halogen, cyano, nitro, amino, hydroxy and in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, alkylcarbonyloxy, alkenylcarbonyloxy, alkynylcarbonyloxy, cycloalkylcarbonyloxy, alkoxycarbonyloxy, alkylsulfonyloxy, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, alkylthio, haloalkylthio, alkenylthio, alkynylthio, cycloalkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxyiminoalkyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminosulfonyl, alkylsulfonylamino, alkylcarbonylamino, alkenylcarbonylamino, alkynylcarbonylamino, cycloalkylcarbonylamino, alkoxycarbonylamino, alkylthiocarbonylamino, bicycloalkyl, aryl, aryloxy, heteroaryl and heteroaryloxy, where the substituents are independently of one another selected from halogen, cyano, nitro, hydroxy, amino, alkyl and haloalkyl,
    R21 represents a radical from the group consisting of hydrogen, alkyl, cycloalkyl, haloalkyl, alkenyl, alkynyl, cycloalkylalkyl, cyanoalkyl, alkylcarbonyl, alkenylcarbonyl, haloalkylcarbonyl, haloalkenylcarbonyl, alkoxyalkyl, alkoxycarbonyl, alkylsulfonyl and haloalkylsulfonyl,
    R23 represents a radical from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, alkylthioalkyl, alkenylthioalkyl, cyanoalkyl, alkoxyalkyl,
    or, if R2 = c) or g),
    R22 and R23 together with the nitrogen atom to which they are attached form a ring which may contain one or more further heteroatoms from the group consisting of nitrogen, oxygen and sulfur, and
    R24 represents hydrogen or an in each case optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, phenyl and phenylalkyl and
    R25 represents hydrogen or an in each case optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, phenyl and phenylalkyl,
    R26 represents a radical from the group consisting of hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkylsulfanyl, haloalkylsulfanyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl and cyanoalkyl.
    R27 represents hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl or cyanoalkyl and compounds of the formula (I) in which
    A represents the A radical
    Figure imgb0501
     where the broken line denotes the bond to the carbon atom of the bicyclic system of the formula (I) and
    G1 represents N or C-B1,
    B1 represents a radical from the group consisting of hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy and in each case optionally substituted cycloalkyl and cycloalkenyl,
    B2 represents a radical from the group consisting of hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy and in each case optionally substituted cycloalkyl and cycloalkenyl,
    T represents oxygen or an electron pair,
    Q represents oxygen or sulfur,
    R1 represents a radical from the group consisting of hydrogen, alkyl, alkoxy and cyano,
    R2 a) represents a B radical from the group consisting of
    Figure imgb0502
    Figure imgb0503
    Figure imgb0504
    Figure imgb0505
    Figure imgb0506
    Figure imgb0507
    Figure imgb0508
    Figure imgb0509
    Figure imgb0510
     where the broken line denotes the bond to the carbon atom of the bicyclic system of the formula (I), or
    R2 c) represents a radical of the formula
    Figure imgb0511
     where the broken line denotes the bond to the carbon atom of the bicyclic system of the formula (I), or
    R2 d) represents a radical of the formula
    Figure imgb0512
     where the broken line denotes the bond to the carbon atom of the bicyclic system of the formula (I), or
    R2 e) represents an F radical from the group consisting of
    Figure imgb0513
    Figure imgb0514
    Figure imgb0515
    Figure imgb0516
     where the broken line denotes the bond to the carbon atom of the bicyclic system of the formula (I), or
    R2 f) represents a radical from the group consisting of haloalkyl and carboxyl,
    R2 g) represents a radical of the formula
    Figure imgb0517
     where the broken line denotes the bond to the carbon atom of the bicyclic system of the formula (I), where
    G2 represents hydrogen or a radical from the group consisting of halogen, nitro, amino, cyano, alkylamino, haloalkylamino, dialkylamino, alkyl, haloalkyl, saturated or unsaturated cycloalkyl which is optionally substituted and optionally interrupted by one or more heteroatoms, cycloalkylalkyl, alkoxy, haloalkoxy, alkoxyalkyl, halogenated alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, bis(alkoxy)alkyl, bis(haloalkoxy)alkyl, alkoxy(alkylsulfanyl)alkyl, alkoxy(alkylsulfinyl)alkyl, alkoxy(alkylsulfonyl)alkyl, bis(alkylsulfanyl)alkyl, bis(haloalkylsulfanyl)alkyl, bis(hydroxyalkylsulfanyl)alkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alpha-hydroxyiminoalkoxycarbonylalkyl, alpha-alkoxyiminoalkoxycarbonylalkyl, C(X2)NR3R4, NR6R7, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, the heterocyclyl radicals dioxanyl, dioxolanyl, dioxepanyl, dioxocanyl, oxathianyl, oxathiolanyl, oxathiepanyl, oxathiocanyl, dithianyl, dithiolanyl, dithiepanyl, dithiocanyl, oxathianyl oxide, oxathiolanyl oxide, oxathiepanyl oxide, oxathiocanyl oxide, oxathianyl dioxide, oxathiolanyl dioxide, oxathiepanyl dioxide, oxathiocanyl dioxide, morpholinyl, triazolinonyl, oxazolinyl, dihydrooxadiazinyl, dihydrodioxazinyl, dihydrooxazolyl, dihydrooxazinyl and pyrazolinonyl (which for their part may be substituted by alkyl, haloalkyl, alkoxy and alkoxyalkyl), phenyl (which for its part may be substituted by halogen, cyano, nitro, alkyl and haloalkyl), the heteroaryl radicals pyridyl, pyridyl N-oxide, pyrimidyl, imidazolyl, pyrazolyl, oxazolyl, thiazolyl, furanyl, thienyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyrazinyl, triazinyl, tetrazinyl and isoquinolinyl (which for their part may be substituted by halogen, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxyalkyl, alkylthio, alkylthioalkyl and cycloalkyl) and the heteroarylalkyl radicals triazolylalkyl, pyridylalkyl, pyrimidylalkyl and oxadiazolylalkyl (which for their part may be substituted by halogen and alkyl), or
    G2 represents a C radical from the group consisting of (C-1) to (C-9)
    Figure imgb0518
    Figure imgb0519
    Figure imgb0520
     where the broken line represents the bond to the B radicals,
    X represents oxygen or sulfur,
    X2 represents oxygen, sulfur, NR5 or NOH,
    L represents oxygen or sulfur,
    V-Z represents R24CH-CHR25 or R24C=CR25,
    n represents 1 or 2,
    m represents 1, 2, 3 or 4,
    R3 represents hydrogen or alkyl,
    R4 represents a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, aryl, arylalkyl and hetarylalkyl,
    R5 represents a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, aryl, arylalkyl and hetarylalkyl, or
    R3 and R4 together with the nitrogen atom to which they are attached form a ring which may contain one or more further heteroatoms from the group consisting of nitrogen, oxygen and sulfur, or
    R3 and R5 together with the nitrogen atoms to which they are attached form a ring,
    R6 represents hydrogen or alkyl,
    R7 represents a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy, haloalkoxy, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkylthioalkyl, aryl, arylalkyl and hetarylalkyl, or
    R6 and R7 together with the nitrogen atom to which they are attached form a ring which may contain one or more further heteroatoms from the group consisting of nitrogen, oxygen and sulfur,
    R8 represents a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkoxy, haloalkoxy, alkenyl, alkoxyalkyl, in each case optionally halogen-substituted alkylcarbonyl and alkylsulfonyl, optionally halogen-substituted alkoxycarbonyl, optionally halogen-, alkyl-, alkoxy-, haloalkyl- and cyano-substituted cycloalkylcarbonyl, or a cation, or an optionally alkyl- or arylalkyl-substituted ammonium ion,
    R9 represents a radical from the group consisting of in each case optionally substituted alkyl, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings may contain at least one heteroatom from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen, in each case optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group,
    R8 and R9 in the radical (C-1), together with the N-S(O)n group to which they are attached, may also form a saturated or unsaturated and optionally substituted 4- to 8-membered ring which may contain one or more further heteroatoms from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen and/or at least one carbonyl group,
    R10 represents hydrogen or alkyl,
    R8 and R10 in the radicals (C-2) and (F-2), together with the nitrogen atoms to which they are attached, may also be a saturated or unsaturated and optionally substituted 4- to 8-membered ring which may contain at least one further heteroatom from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen and/or at least one carbonyl group,
    R9 and R10 in the radicals (C-2) and (F-2) may also form, together with the N-S(O)n group to which they are attached, a saturated or unsaturated and optionally substituted 4- to 8-membered ring which may contain one or more further heteroatoms from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen and/or at least one carbonyl group,
    R11 represents an in each case optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyl, cycloalkyloxy, cycloalkenyloxy, cycloalkylalkoxy, alkylthio, alkenylthio, phenoxy, phenylthio, benzyloxy, benzylthio, heteroaryloxy, heteroarylthio, heteroarylalkoxy and heteroarylalkylthio,
    R12 represents an in each case optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyl, cycloalkyloxy, cycloalkenyloxy, cycloalkylalkoxy, alkylthio, alkenylthio, phenoxy, phenylthio, benzyloxy, benzylthio, heteroaryloxy, heteroarylthio, heteroarylalkoxy and heteroarylalkylthio,
    R11 and R12 in the radicals (C-3) and (F-3) may also form, together with the phosphorus atom to which they are bonded, a saturated or unsaturated and optionally substituted 5- to 7-membered ring which may contain one or two heteroatoms from the group consisting of oxygen (where oxygen atoms must not be directly adjacent to one another) and sulfur,
    R13 represents an in each case optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, phenyl and phenylalkyl,
    R14 represents an in each case optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, phenyl and phenylalkyl,
    R15 represents a radical from the group consisting of in each case optionally substituted alkyl, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings may contain at least one heteroatom from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen, in each case optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group,
    R8 and R15 in the radicals (C-6) and (F-6) may also form, together with the N-S(O)n group to which they are attached, a saturated or unsaturated and optionally substituted 4- to 8-membered ring which may contain one or more further heteroatoms from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen and/or at least one carbonyl group,
    R16 represents a radical from the group consisting of hydrogen, in each case optionally substituted alkyl, alkoxy, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings may contain at least one heteroatom from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen, in each case optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group,
    R8 and R16 in the radicals (C-7) and (F-7) may also form, together with the nitrogen atom to which they are attached, a saturated or unsaturated and optionally substituted 4- to 8-membered ring which may contain one or more further heteroatoms from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen and/or at least one carbonyl group,
    R17 represents a radical from the group consisting of in each case optionally substituted alkyl, alkoxy, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings may contain at least one heteroatom from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen, in each case optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group,
    R8 and R17 in the radicals (C-8) and (F-8) may also form, together with the N-C(X) group to which they are attached, a saturated or unsaturated and optionally substituted 4- to 8-membered ring which may contain one or more further heteroatoms from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen and/or at least one carbonyl group,
    Y1 and Y2 independently of one another represent C=O or S(O)2,
    R22 in the case that R2 represents g), represents a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, optionally halogen-substituted alkoxyalkyl, optionally halogen-substituted bis(alkoxy)alkyl, optionally halogen-substituted alkylsulfanylalkyl, optionally halogen-substituted alkylcarbonylalkyl, optionally halogen-substituted alkylsulfinylalkyl, optionally halogen-substituted alkylsulfonylalkyl, dialkylaminosulfanylalkyl, dialkylaminosulfinylalkyl, dialkylaminosulfonylalkyl, optionally halogen-substituted alkoxycarbonylalkyl, optionally halogen-substituted alkynyloxy, dialkylaminocarbonylalkyl, N-alkyl-N-cycloalkylaminocarbonylalkyl, heterocyclylcarbonylalkyl, alkylsulfanyl, haloalkylsulfanyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, cycloalkyl which is optionally substituted by halogen, cyano, nitro, alkyl, cycloalkyl, haloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, haloalkoxycarbonyl or hetaryl (which for its part is optionally substituted by alkyl or halogen), cycloalkylalkyl which is optionally substituted by halogen, cyano, nitro, alkyl, haloalkyl, cycloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, haloalkoxycarbonyl or hetaryl (which for its part is optionally substituted by alkyl or halogen), optionally substituted heterocyclyl, heterocyclylalkyl which is optionally substituted by halogen, cyano (also in the alkyl moiety), nitro, hydroxy, alkyl, haloalkyl, cycloalkyl (which is optionally substituted), alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulpinyl, alkylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, amino, alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonylamino, alkoxyalkyl, haloalkoxyalkyl, alkenyl, alkynyl, cycloalkylalkyl, alkylcarbonyl, alkoxycarbonyl or aminocarbonyl, aryl which is optionally substituted by halogen, cyano, nitro, hydroxy, amino, alkyl, haloalkyl, cycloalkyl (which is optionally substituted), alkoxy or haloalkoxy, arylalkyl which is optionally substituted by halogen, cyano (also in the alkyl moiety), nitro, hydroxy, amino, alkyl, cycloalkyl (which is optionally substituted), haloalkyl, alkoxy or haloalkoxy, hetarylalkyl which is optionally substituted by halogen, cyano (also in the alkyl moiety), nitro, hydroxy, alkyl, haloalkyl, cycloalkyl (which is optionally substituted), alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, amino, alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonylamino, alkoxyalkyl, haloalkoxyalkyl, alkenyl, alkynyl, cycloalkylalkyl, alkylcarbonyl, alkoxycarbonyl or aminocarbonyl, or, in the case that R2 represents c), d) or g),
    R22 represents a D radical from the group consisting of (D-1) to (D-3)
    Figure imgb0521
     in which
    X1 represents a radical from the group consisting of hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, cycloalkyl, alkoxy and haloalkoxy,
    R represents NR18R19, or represents an in each case optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, alkoxyalkyl, alkyl-S-alkyl, alkyl-S(O)-alkyl, alkyl-S(O)2-alkyl, R18-CO-alkyl, NR18R19-CO-alkyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, phenyl, phenylalkyl, hetaryl and hetarylalkyl,
    Y3 represents a radical from the group consisting of hydrogen, halogen, cyano, alkyl, cycloalkyl, haloalkyl, alkoxy, haloalkoxy and NR20R21,
    W represents a radical from the group consisting of O, S, SO and SO2,
    R22 furthermore represents an E radical from the group consisting of (E-1) to (E-11)
    Figure imgb0522
    Figure imgb0523
    Figure imgb0524
     of the group consisting of (E-18) to (E-51)
    Figure imgb0525
    Figure imgb0526
    Figure imgb0527
    Figure imgb0528
    Figure imgb0529
    Figure imgb0530
    Figure imgb0531
    Figure imgb0532
    Figure imgb0533
    Figure imgb0534
     or, in the case that R2 = d),
    R22 also represents an E radical from the group consisting of E-12 to E-17
    Figure imgb0535
    Figure imgb0536
    R18 represents a radical from the group consisting of hydrogen, hydroxy, in each case optionally substituted alkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkylcarbonyl, alkoxycarbonyl, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl, cycloalkenyl and cycloalkenylalkyl, in which the rings may contain at least one heteroatom from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen, in each case optionally substituted aryl, arylalkyl, heteroaryl and heteroarylalkyl and an optionally substituted amino group,
    R19 represents a radical from the group consisting of hydrogen, represents an alkali metal or alkaline earth metal ion or represents an ammonium ion which is optionally mono- to tetrasubstituted by C1-C4-alkyl or represents an in each case optionally halogen- or cyano-substituted radical from the group consisting of alkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl and alkylsulfonylalkyl,
    R20 represents a radical from the group consisting of hydrogen, halogen, cyano, nitro, amino, hydroxy and in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, alkylcarbonyloxy, alkenylcarbonyloxy, alkynylcarbonyloxy, cycloalkylcarbonyloxy, alkoxycarbonyloxy, alkylsulfonyloxy, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, alkylthio, haloalkylthio, alkenylthio, alkynylthio, cycloalkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxyiminoalkyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminosulfonyl, alkylsulfonylamino, alkylcarbonylamino, alkenylcarbonylamino, alkynylcarbonylamino, cycloalkylcarbonylamino, alkoxycarbonylamino, alkylthiocarbonylamino, bicycloalkyl, aryl, aryloxy, heteroaryl and heteroaryloxy, where the substituents are independently of one another selected from halogen, cyano, nitro, hydroxy, amino, alkyl and haloalkyl,
    R21 represents a radical from the group consisting of hydrogen, alkyl, cycloalkyl, haloalkyl, alkenyl, alkynyl, cycloalkylalkyl, cyanoalkyl, alkylcarbonyl, alkenylcarbonyl, haloalkylcarbonyl, haloalkenylcarbonyl, alkoxyalkyl, alkoxycarbonyl, alkylsulfonyl and haloalkylsulfonyl,
    R23 represents a radical from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, alkylthioalkyl, alkenylthioalkyl, cyanoalkyl, alkoxyalkyl,
    or, if R2 = g),
    R22 and R23 together with the nitrogen atom to which they are attached form a ring which may contain one or more further heteroatoms from the group consisting of nitrogen, oxygen and sulfur, and
    R24 represents hydrogen or an in each case optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, phenyl and phenylalkyl and
    R25 represents hydrogen or an in each case optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, phenyl and phenylalkyl,
    R26 represents a radical from the group consisting of hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkylsulfanyl, haloalkylsulfanyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl and cyanoalkyl.
    R27 represents hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl or cyanoalkyl.
  2. Compounds of the formula (I) according to Claim 1, in which
    A represents the A radical (A-a)
    Figure imgb0537
     where the broken line denotes the bond to the carbon atom of the bicyclic system of the formula (I),
    G1 represents C-B1,
    B1 represents hydrogen,
    B2 represents hydrogen,
    T represents an electron pair,
    R1 represents hydrogen,
    R2 a) represents one of the radicals below
    Figure imgb0538
    Figure imgb0539
     where the broken line denotes the bond to the carbon atom of the bicyclic system of the formula (I), or
    R2 c) represents a radical of the formula
    Figure imgb0540
     where the broken line denotes the bond to the carbon atom of the bicyclic system of the formula (I), or
    R2 d) represents a radical of the formula
    Figure imgb0541
     where the broken line denotes the bond to the carbon atom of the bicyclic system of the formula (I), or
    R2 f) represents C1-C6-haloalkyl or
    R2 g) represents a radical of the formula
    Figure imgb0542
     where the broken line in each case denotes the bond to the carbon atom of the bicyclic system of the formula (I), in which
    G2 represents a radical from the group consisting of hydrogen, C1-C4-alkyl and halo-C1-C4-alkyl,
    R22 in the case that R2 represents g), represents a radical from the group consisting of methyl, ethyl, isopropyl, n-propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, 2,2-difluoro-n-propyl, methylsulfanylmethyl, methylsulfanylethyl, methylsulfanyl-n-propyl, methylsulfonyl, ethylsulfonyl, methylsulfonylmethyl, ethylsulfonylmethyl, isopropylsulfonylmethyl, cyclopropyl and, in the case that R2 represents c), d) or g),
    R22 represents (D-2)
    Figure imgb0543
     in which
    X1 represents a radical from the group consisting of hydrogen, fluorine, chlorine and bromine,
    R represents C1-C4-alkyl, optionally mono-, di-, tri-, tetra- or pentasubstituted by fluorine, chlorine,
    W represents a radical from the group consisting of S, SO and SO2,
    Y3 represents hydrogen or methyl and
    R23 represents hydrogen or C1-C6-alkyl or, in the case that R2 represents g),
    R22 and R23 together with the nitrogen atom to which they are attached represent pyrrolidinyl or morpholinyl.
  3. Composition, characterized by a content of at least one compound of the formula (I) according to either of Claims 1 and 2 and customary extenders and/or surfactants.
  4. Non-therapeutic use of compounds of the formula (I) according to either of Claims 1 and 2 or of compositions according to Claim 3 for controlling pests.
  5. Compound of the formula
    Figure imgb0544
EP15801879.6A 2014-12-02 2015-12-01 Bicyclic compounds as pest controllers Not-in-force EP3227303B1 (en)

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US10383335B2 (en) 2015-04-09 2019-08-20 Fmc Corporation Bicyclic pyrazole pesticides
MX2019003136A (en) * 2016-09-19 2019-07-18 Bayer Cropscience Ag Pyrazolo [1,5-a]pyridine derivatives and their use as pesticides.
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